Chang, Y.-C.; Huang, H.-P.; Hsu, J.-D.; Yang, S.-F.; Wang, C.-J. . E-mail: email@example.com
Hibiscus sabdariffa Linne (Malvaceae), an attractive plant believed to be native to Africa, is cultivated in the Sudan and Eastern Taiwan. Anthocyanins exist widely in many vegetables and fruits. Some reports demonstrated that anthocyanins extracted from H. sabdariffa L., Hibiscus anthocyanins (HAs) (which are a group of natural pigments existing in the dried calyx of H. sabdariffa L.) exhibited antioxidant activity and liver protection. Therefore, in this study, we explored the effect of HAs on human cancer cells. The result showed that HAs could cause cancer cell apoptosis, especially in HL-60 cells. Using flow cytometry, we found that HAs treatment (0-4 mg/ml) markedly induced apoptosis in HL-60 cells in a dose- and time-dependent manner. The result also revealed increased phosphorylation in p38 and c-Jun, cytochrome c release, and expression of tBid, Fas, and FasL in the HAs-treated HL-60 cells. We further used SB203580 (p38 inhibitor), PD98059 (MEK inhibitor), SP600125 (JNK inhibitor), and wortmannin (phosphatidylinositol 3-kinase; PI-3K inhibitor) to evaluate their effect on the HAs-induced HL-60 death. The data showed that only SB203580 had strong potential in inhibiting HL-60 cell apoptosis and related protein expression and phosphorylation. Therefore, we suggested that HAs mediated HL-60 apoptosis via the p38-FasL and Bid pathway. According to these results, HAs could be developed as chemopreventive agents. However, further investigations into the specificity and mechanism(s) of HAs are needed.
Lo, Chia-Wen; Huang, Hui-Pei; Lin, Hui-Mei; Chien, Cheng-Ting; Wang, Chau-Jong
Hibiscus sabdariffa L. (Malvaceae), an attractive plant believed to be native to Africa, is cultivated in Sudan and in eastern Taiwan. It has been reported to contain a number of protocatechuic acid and anthocyanins. In vitro experimental studies have shown that anthocyanins administration of the extract produces anti-inflammation and chemoprevention effects. In spite of the wide use of Hibiscus sabdariffa L. in folk medicine for treating various diseases, our previous study indicated a potency of Hibiscus sabdariffa extract (HSE) in anti-atherosclerosis. The mechanisms of anthocyanins administration of the extract produce from Hibiscus sabdariffa L. to attenuate atherosclerosis were not clarified. In this study, we found that Hibiscus anthocyanins (HAs) could inhibit the serum-stimulated proliferation of smooth muscle cell (SMC) and result in cell apoptosis. The HAs inducing cell apoptosis was dose dependent. We further used SB203580 (p38 inhibitor) to block cellular apoptosis and evaluate its effect on the HAs-inducing SMC death via some apoptosis criteria including DNA fragmentation and flow cytometry. We suggested that the mechanisms of the inhibitory effect of HAs on atherosclerosis could be via inhibiting the proliferation of SMC. HAs induces apoptosis via (i) activating p38 MAP kinase that subsequently phosphorylates target protein c-Jun and transduces the signal to further activate the apoptotic protein cascades that contain Fas-mediated signaling (Fas/caspase-8 signaling module) and (ii) activating p53 and inducing bax expression. As an outcome of the events, cytochrome c releases from the mitochondria, leading to cell apoptosis. In these experiments, HAs showed strong potential to induce SMC cell apoptosis via p38 and p53 pathway. In consequence, the rate of atherosclerotic formation is slowed down, and the progress is suppressed.
Anthocyanins are one type of flavonoid phytopigment. Although the role of anthocyanins as a functional food factor remains relatively less established than that of other flavonoids, progress in this area has been made at the molecular level in recent years. This review discusses the potential health benefits of plant-derived anthocyanin-rich foods, with a focus on the role of anthocyanins in obesity control, diabetes control, cardiovascular disease prevention, and improvement of visual and brain functions, areas that have attracted much attention. Such health benefits are not necessarily derived from the antioxidant effect of anthocyanins, but in fact are produced by currently unestablished chemical properties beyond the antioxidant capacity of the molecules. However, a better understanding of the physiological functionality of anthocyanins remains to be elucidated. It is desirable, therefore, to clarify the molecular type and composition of the anthocyanins that confer specific health benefits and to conduct further investigation into the underlying molecular mechanisms. The pharmacological actions of anthocyanins could not be fully established without knowledge on the effects of treatment of anthocyanins alone, the effects of non-anthocyanin components, and the possible interactions between anthocyanin and non-anthocyanin species. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Lin, Z; Fischer, J; Wicker, L
Pectin was extracted from blueberry powder into three fractions of water soluble (WSF), chelator soluble (CSF) and sodium carbonate soluble (NSF). The fractions were incubated with cyanidin-3-glucoside (C3G), a mixture of five anthocyanidins (cyanidin, pelargonidin, malvidin, petunidin and delphinidin) or blueberry juice at pH 2.0-4.5. Free anthocyanins and bound anthocyanin-pectin mixtures were separated by ultrafiltration. WSF bound the least amount of anthocyanin at all pH values. CSF had stronger anthocyanin binding ability at pH 2.0-3.6, while NSF had stronger anthocyanin binding ability at pH 3.6-4.5. The pectin and anthocyanin binding was lowest at pH 4.5 and higher at pH 2.0-3.6. Nearly doubling C3G pigment content increased bound anthocyanin percentage by 16-23% at pH 3.6, which favored anthocyanin aromatic stacking, compared to 3-9% increase at pH 2.0. Ionic interaction between anthocyanin flavylium cations and free pectic carboxyl groups, and anthocyanin stacking may be two major mechanisms for pectin and anthocyanin binding. Copyright © 2015 Elsevier Ltd. All rights reserved.
Grace, Mary H; Ribnicky, David M; Kuhn, Peter; Poulev, Alexander; Logendra, Sithes; Yousef, Gad G; Raskin, Ilya; Lila, Mary Ann
Blueberry fruits are known as a rich source of anthocyanin components. In this study we demonstrate that anthocyanins from blueberry have the potency to alleviate symptoms of hyperglycemia in diabetic C57b1/6J mice. The anti-diabetic activity of different anthocyanin-related extracts was evaluated using the pharmaceutically acceptable self-microemulsifying drug delivery system: Labrasol. Treatment by gavage (500 mg/kg body wt) with a phenolic-rich extract and an anthocyanin-enriched fraction formulated with Labrasol lowered elevated blood glucose levels by 33 and 51%, respectively. The hypoglycemic activities of these formulae were comparable to that of the known anti-diabetic drug metformin (27% at 300 mg/kg). The extracts were not significantly hypoglycemic when administered without Labrasol, demonstrating its bio-enhancing effect, most likely due to increasing the bioavailability of the administered preparations. The phenolic-rich extract contained 287.0+/-9.7 mg/g anthocyanins, while the anthocyanin-enriched fraction contained 595+/-20.0 mg/g (cyanidin-3-glucoside equivalents), as measured by HPLC and pH differential analysis methods. The greater hypoglycemic activity of the anthocyanin-enriched fraction compared to the initial phenolic-rich extract suggested that the activity was due to the anthocyanin components. Treatment by gavage (300 mg/kg) with the pure anthocyanins, delphinidin-3-O-glucoside and malvidin-3-O-glucoside, formulated with Labrasol, showed that malvidin-3-O-glucoside was significantly hypoglycemic while delphinidin-3-O-glucoside was not.
Grace, Mary H.; Ribnicky, David M.; Kuhn, Peter; Poulev, Alexander; Logendra, Sithes; Yousef, Gad G.; Raskin, Ilya; Lila, Mary Ann
Blueberry fruits are known as a rich source of anthocyanin components. In this study we demonstrate that anthocyanins from blueberry have the potency to alleviate symptoms of hyperglycemia in diabetic C57b1/6J mice. The anti-diabetic activity of different anthocyanin-related extracts was evaluated using the pharmaceutically acceptable self-microemulsifying drug delivery system; Labrasol. Treatment by gavage (500 mg/kg body wt) with a phenolic-rich extract and an anthocyanin-enriched fraction formulated with Labrasol lowered elevated blood glucose levels by 33 and 51%, respectively. The hypoglycemic activities of these formulae were comparable to that of the known anti-diabetic drug metformin (Baily and Day, 2004; 27% at 300 mg/kg). The extracts were not significantly hypoglycemic when administered without Labrasol, demonstrating its bio-enhancing effect, most likely due to increasing the bioavailability of the administered preparations. The phenolic-rich extract contained 287.0 ± 9.7 mg/g anthocyanins, while the anthocyanin-enriched fraction contained 595 ± 20.0 mg/g (cyanidin-3-glucoside equivalents), as measured by HPLC and pH differential analysis methods. The greater hypoglycemic activity of the anthocyanin-enriched fraction compared to the initial phenolic-rich extract suggested that the activity was due to the anthocyanin components. Treatment by gavage (300 mg/kg) with the pure anthocyanins, delphinidin-3-O-glucoside and malvidin-3-O- glucoside, formulated with Labrasol, showed that malvidin-3-O- glucoside was significantly hypoglycemic while delphinidin-3-O-glucoside was not. PMID:19303751
Ghosh, Dilip; Konishi, Tetsuya
Anthocyanins are the largest group of water-soluble pigments in the plant kingdom, known collectively as flavonoids. More than 8000 flavonoids, and 500 anthocyanin structures had been reported by the year 2000 and more are continually being isolated. Anthocyanins are believed to display an array of beneficial actions on human health and well-being. Due to our increasing understanding and awareness of the potential beneficial human health effects, research on anthocyanins has recently intensified. During the past two decades an increasing number of studies have investigated the diverse protective effects elicited by polyphenolics present in various fruits and vegetables. These effects include antioxidant, anti-allergic, anti-inflammatory, anti-viral, antiproliferative, anti-mutagenic, anti-microbial, anti-carcinogenic, protection from cardiovascular damage and allergy, microcirculation improvement, peripheral capillary fragility prevention, diabetes prevention, and vision improvement. Other physiological effects are continually being investigated. The aim of the present article is to summarise the known anti-diabetic and eye function properties of anthocyanins to help in our understanding of their functional mechanism.
Diaconeasa, Zoriţa; Leopold, Loredana; Rugină, Dumitriţa; Ayvaz, Huseyin; Socaciu, Carmen
The present study was aimed at evaluating the antiproliferative potential of anthocyanin-rich fractions (ARFs) obtained from two commercially available juices (blueberry and blackcurrant juices) on three tumor cell lines; B16F10 (murine melanoma), A2780 (ovarian cancer) and HeLa (cervical cancer). Individual anthocyanin determination, identification and quantification were done using HPLC-MS. Antioxidant activity of the juices was determined through different mechanism methods such as DPPH and ORAC. For biological testing, the juices were purified through C18 cartridges in order to obtain fractions rich in anthocyanins. The major anthocyanins identified were glycosylated cyanidin derivatives. The antiproliferative activity of the fractions was tested using the MTT assay. The antiproliferative potential of ARF was found to be associated with those bioactive molecules, anthocyanins due to their antioxidant potential. The results obtained indicated that both blueberry and blackcurrants are rich sources of antioxidants including anthocyanins and therefore these fruits are highly recommended for daily consumption to prevent numerous degenerative diseases. PMID:25622252
Diaconeasa, Zoriţa; Leopold, Loredana; Rugină, Dumitriţa; Ayvaz, Huseyin; Socaciu, Carmen
The present study was aimed at evaluating the antiproliferative potential of anthocyanin-rich fractions (ARFs) obtained from two commercially available juices (blueberry and blackcurrant juices) on three tumor cell lines; B16F10 (murine melanoma), A2780 (ovarian cancer) and HeLa (cervical cancer). Individual anthocyanin determination, identification and quantification were done using HPLC-MS. Antioxidant activity of the juices was determined through different mechanism methods such as DPPH and ORAC. For biological testing, the juices were purified through C18 cartridges in order to obtain fractions rich in anthocyanins. The major anthocyanins identified were glycosylated cyanidin derivatives. The antiproliferative activity of the fractions was tested using the MTT assay. The antiproliferative potential of ARF was found to be associated with those bioactive molecules, anthocyanins due to their antioxidant potential. The results obtained indicated that both blueberry and blackcurrants are rich sources of antioxidants including anthocyanins and therefore these fruits are highly recommended for daily consumption to prevent numerous degenerative diseases.
Miyake, Seiji; Takahashi, Noriko; Sasaki, Mariko; Kobayashi, Saori; Tsubota, Kazuo; Ozawa, Yoko
Anthocyanin-rich bilberry extract, a plant-derived antioxidant, has been utilized as a popular supplement for ocular health worldwide. However, it is unclear whether this extract has any biological effect on visual function, and the mechanism for such an effect is completely unknown. In this study, we generated a mouse model of endotoxin-induced uveitis (EIU) that shows retinal inflammation, as well as uveitis, by injecting lipopolysaccharide. We pretreated the mice with anthocyanin-rich bilberry extract and analyzed the effect on the retina. Anthocyanin-rich bilberry extract prevented the impairment of photoreceptor cell function, as measured by electroretinogram. At the cellular level, we found that the EIU-associated rhodopsin decreased and the shortening of outer segments in photoreceptor cells were suppressed in the bilberry-extract-treated animals. Moreover, the extract prevented both STAT3 activation, which induces inflammation-related rhodopsin decrease, and the increase in interleukin-6 expression, which activates STAT3. In addition to its anti-inflammatory effect, the anthocyanin-rich bilberry extract ameliorated the intracellular elevation of reactive oxygen species and activated NF-κB, a redox-sensitive transcription factor, in the inflamed retina. Our findings indicate that anthocyanin-rich bilberry extract has a protective effect on visual function during retinal inflammation.
Mojica, Luis; Berhow, Mark; Gonzalez de Mejia, Elvira
Black beans contain anthocyanins that could be used as colorants in foods with associated health benefits. The objective was to optimize anthocyanins extraction from black bean coats and evaluate their physicochemical stability and antidiabetes potential. Optimal extraction conditions were 24% ethanol, 1:40 solid-to-liquid ratio and 29°C (P<0.0001). Three anthocyanins were identified by MS ions, delphinidin-3-O-glucoside (465.1m/z), petunidin-3-O-glucoside (479.1m/z) and malvidin-3-O-glucoside (493.1m/z). A total of 32mg of anthocyanins were quantified per gram of dry extract. Bean anthocyanins were stable at pH 2.5 and low-temperature 4°C (89.6%), with an extrapolated half-life of 277days. Anthocyanin-rich extracts inhibited α-glucosidase (37.8%), α-amylase (35.6%), dipeptidyl peptidase-IV (34.4%), reactive oxygen species (81.6%), and decreased glucose uptake. Black bean coats are a good source of anthocyanins and other phenolics with the potential to be used as natural-source food colorants with exceptional antidiabetes potential. Copyright © 2017 Elsevier Ltd. All rights reserved.
Janšáková, Katarína; Bábíčková, Janka; Havrlentová, Michaela; Hodosy, Július; Kraic, Ján; Celec, Peter; Tóthová, Ľubomíra
Aim To evaluate the effect of food containing anthocyanin-rich wheat on oxidative status and behavior of healthy rats. Methods Twenty male rats were divided into the control and anthocyanin group. Oral glucose tolerance test was performed, and proteinuria and creatinine clearance were measured. Behavioral analysis was performed in Phenotyper cages. Serum and tissues were collected to measure the markers of oxidative stress and antioxidant status. Results Anthocyanins significantly increased total antioxidant capacity in serum (P = 0.039), decreased advanced oxidation protein products in the kidney (P = 0.002), but increased thiobarbituric acid reactive substances in the kidney compared to the control group. No significant difference between the groups was found in the markers of oxidative stress in the liver and colon, as well as in renal functions and glucose metabolism. The anthocyanin group spent significantly less time in the spotlight zone of the Phenotyper cages (P = 0.040), indicating higher anxiety-like behavior. Conclusion Food containing anthocyanin-rich wheat had positive effects on serum antioxidant status and kidney protein oxidation, but increased lipid peroxidation in the kidney and modified animal behavior related to anxiety. The molecular mechanisms leading to observed effects should be further elucidated. PMID:27106354
Díaz-García, Miriam Cristina; Castellar, María Rosario; Obón, José María; Obón, Concepción; Alcaraz, Francisco; Rivera, Diego
Anthocyanins and other polyphenols from flowers and bracts of Thymus sp. are studied. An anthocyanin-rich food colourant with interesting high antioxidant activity from Thymus moroderi has been obtained, and applied to colour foods. Anthocyanins and other polyphenols from T. moroderi and another five Thymus sp. were extracted in methanol/hydrochloric acid 0.1 mol L(-1) (50/50, v/v) 2 h stirring at 50 °C. They were identified and quantified by HPLC-PDA-MS and UHPLC-PDA-fluorescence, as total individual polyphenols. Total polyphenols were also determined. Flowers had higher anthocyanins and other polyphenols concentrations than bracts; for example, total polyphenols content of T. moroderi were 131.58 and 61.98 g GAE kg(-1) vegetal tissue, respectively. A liquid concentrated colourant was obtained from T. moroderi using water/citric acid as solvent. It was characterised and compared with other two commercial anthocyanin-rich food colourants from red grape skin and red carrot (colour strength of 1.7 and 3.6 AU, respectively). T. moroderi colourant had 1.2 AU colour strength, and high storage stability (>97.1% remaining colour after 110 days at 4 °C). It showed a higher polyphenols content than commercial colourants. Its antioxidant activity was 0.707 mmol Trolox eq. g(-1) plant dry weight, 69.5 times higher than red carrot. The three colourants were applied to colour yogurts, giving pinky tonalities. The colour did not change evidently (ΔE*(ab) < 3) when stored under refrigeration during 1 month. T. moroderi can be a source of anthocyanin-rich food colourant (E-163) with both high polyphenols content and high antioxidant activity. This colourant gives a stable colour to a yogurt during 1 month. These results expand the use of natural colourants. © 2014 Society of Chemical Industry.
Hosoda, Kenji; Eruden, Bayaru; Matsuyama, Hiroki; Shioya, Shigeru
Anthocyanin in purple corn (Zea mays L.) has been reported to show several functional and biological attributes, displaying antioxidant, antiobesity and antidiabetic effects in monogastric animals. The objective of this study was to investigate the effect of feeding anthocyanin-rich corn (Zea mays L., Choko C922) silage on digestibility, milk production and plasma enzyme activities in lactating dairy cows. The cows were fed diets based on the control corn or the anthocyanin-rich corn silage (AR treatment) in a crossover design. The anthocyanin-rich corn silage-based diet had a lower starch content, nutrient digestibility and total digestible nutrients content when compared to the control diet. The milk yield, lactose and solids-not-fat contents in the AR-treatment cows were lower than in the control cows. The feeding of the anthocyanin-rich corn silage led to a reduction in aspartate aminotransferase (AST) activity and an increase in superoxide dismutase (SOD) activity in the plasma. These data suggest that the anthocyanin-rich corn has a lowering effect on AST activity with concomitant enhancement of SOD activity in lactating dairy cows. However, a new variety of anthocyanin-rich corn with good nutritional value is needed for practical use as a ruminant feed.
Juadjur, A; Mohn, C; Schantz, M; Baum, M; Winterhalter, P; Richling, E
The incidence of chronic diseases increases with advancing age of the population. A commonly discussed cause of chronic diseases is oxidative stress, which occurs in the body when there is an imbalance between the formation and inactivation of so-called reactive oxygen species (ROS). Epidemiological data suggest that a 'healthy diet', with a high content of flavonoids indicates preventive properties and correlates with an inverse effect with respect to the risk of chronic diseases. Berries (especially bilberries, Vaccinium myrtillus L.) are an important source of these flavonoids. In this study, we investigated, in vitro, the antioxidative properties of fractions obtained from a commercially available anthocyanin-rich bilberry extract (BE). As markers for antioxidative activity, the intracellularly generated ROS levels, oxidative DNA damage, and total glutathione (tGSH) levels were determined in the human colon cell lines Caco-2 and HT-29. In Caco-2 cells, the ROS levels and, in both cell lines, the oxidative DNA damage, were significantly reduced in the presence of the original BE and phenolcarbonic acid-rich fraction. Total GSH levels were slightly increased after pretreatment with BE, phenolcarbonic acid and the polymeric fractions, but not with the anthocyanin fraction. In summary, the BE and the therefrom-isolated phenolcarbonic acid-rich fraction, showed the most potent antioxidative activity whereas the polymeric and anthocyanin-rich fraction, in total, were less active. Copyright © 2014 Elsevier Ltd. All rights reserved.
Maeda-Yamamoto, Mari; Saito, Takeshi; Nesumi, Atsushi; Tokuda, Yoshiko; Ema, Kaori; Honma, Daiki; Ogino, Akiko; Monobe, Manami; Murakami, Akira; Murakami, Akira; Tachibana, Hirofumi
The purpose of this study was to evaluate the effects of leaf order or crop season on anthocyanins and other chemicals in the anthocyanin-rich tea cultivar 'Sunrouge' (Camellia sinensis x C. taliensis) by using high-performance liquid chromatography, and to study the effect of 'Sunrouge' extract on acetylcholinesterase (AChE) activity in human neuroblastoma SK-N-SH cells. The total anthocyanin content was higher in the third (3.09 mg g⁻¹) than in the second (2.24 mg g⁻¹) or first crop season (1.79 mg g⁻¹). The amount of anthocyanins contained in the stem was high (1.61 mg g⁻¹). In the third crop season, the concentrations of delphinidin-3-O-β-D-(6-(E)-p-coumaroyl)galactopyranoside (DCGa), cyanidin-3-O-β-D-(6-(E)-p-coumaroyl)galactopyranoside, delphinidin-3-O-β-D-galactopyranoside, delphinidin-3-O-β-D-(6-O-(Z)-p-coumaroyl)galactopyranoside, cyanidin-3-O-β-D-galactoside, and delphinidin-3-O-β-D-glucoside were 1.57 mg g⁻¹, 0.52 mg g⁻¹, 0.40 mg g⁻¹, 0.22 mg g⁻¹, 0.14 mg g⁻¹, and 0.11 mg g⁻¹, respectively. DCGa accounted for about 50% of the anthocyanins present. The suppressive effect of 'Sunrouge' water extract on AChE activity in human neuroblastoma SK-N-SH cells was the strongest among the three tea cultivars ('Sunrouge', 'Yabukita' and 'Benifuuki'). These results suggested that 'Sunrouge' might protect humans from humans from AChE-related diseases by suppressing AChE activity. To obtain sufficient amounts of anthocyanins, catechins and/or caffeine for a functional food material, 'Sunrouge' from the third crop season should be used. Copyright © 2012 Society of Chemical Industry.
Bobe, Gerd; Wang, Bing; Seeram, Navindra P; Nair, Muraleedharan G; Bourquin, Leslie D
A promising approach for cancer chemoprevention might be a combination therapy utilizing dietary phytochemicals and anticarcinogenic pharmaceuticals at a suboptimal dosage to minimize any potential adverse side effects. To test this hypothesis, various dosages of anthocyanin-rich tart cherry extract were fed in combination with suboptimal levels of the nonsteroidal anti-inflammatory drug sulindac to APCMin mice for 19 weeks. By the end of the feeding period, fewer mice that were fed the anthocyanin-rich extract in combination with sulindac lost more than 10% of body weight than mice fed sulindac alone. Mice that were fed anthocyanin-rich extract (at any dose) in combination with sulindac had fewer tumors and a smaller total tumor burden (total tumor area per mouse) in the small intestine when compared to mice fed sulindac alone. These results suggest that a dietary combination of tart cherry anthocyanins and sulindac is more protective against colon cancer than sulindac alone.
Jing, Pu; Giusti, M Mónica
Pigment production from anthocyanin-rich purple corncobs generates a deeply colored waste precipitate. Our objectives were to characterize this anthocyanin-rich waste (ARW) and to find a suitable application in a food matrix. Composition and solubility characteristics of ARW were evaluated. Color (CIELAB) and pigment (monomeric anthocyanin and HPLC profiles) stability of ARW in milk (35 mg/100 mL) were evaluated using an accelerated test at 70 degrees C and phosphate buffer as a control. ARW provided milk an attractive purple hue (324-347 degrees ). Monomeric anthocyanin degradation followed zero-order kinetics in skim and whole milk and second-order kinetics in the control, with half-lives of 173, 223, and 44 min at 70 degrees C, respectively. ARW shows potential as a natural colorant for a pH range unusual for anthocyanin applications. A protective effect of matrix constituents on the stability of anthocyanins was evident. Anthocyanins may interact with different compounds in biological systems when the pH values are close to neutral.
Kuntz, Sabine; Kunz, Clemens; Rudloff, Silvia
Pancreatic cancer is an aggressive cancer type, of which the most important characteristics are migration and metastasis. Anthocyanins (ACN) are discussed to be protective phytochemicals; however, up to now only scarce data are available regarding their effects on cancer prevention. In this study, we aimed to determine whether ACN and their metabolites from plasma (PAM), isolated from blood of healthy volunteers after ingestion of an ACN-rich juice, are effective in modulating cancer cell migration in vitro. PAM were isolated from blood of healthy volunteers (n = 10) after consumption of an ACN-rich berry juice. Before ingestion (PAM0min) and after 60 min (PAM60min), blood was taken and PAM were isolated from plasma by solid-phase extraction. Migration of pancreatic cancer cells PANC-1 and AsPC-1 was assayed in a Boyden chamber. The influence of PAM on cellular reactive oxygen species (ROS) or mitochondria-specific ROS was measured fluorimetrically. mRNA expression levels of matrix metalloproteinases (MMP-2 and MMP-9) and NF-κB mRNA were determined by real-time PCR. After application of PAM60min to PANC-1, we observed a reduced cell migration, which was associated with reduced levels of endogenously generated ROS concomitant with reduced NF-κB as well as MMP-2 and MMP-9 mRNA expression levels. In AsPC-1 cells, however, migration was not affected by PAM60min. It can be assumed that physiologically relevant ACN and their metabolites were able to inhibit pancreatic cancer cell migration in dependency of the phenotype of cells and may thus deserve further attention as potential bioactive phytochemicals in cancer prevention.
Lala, Geeta; Malik, Minnie; Zhao, Cuiwei; He, Jian; Kwon, Youngjoo; Giusti, M Monica; Magnuson, Bernadene A
The aim of the present study was to investigate the chemoprotective activity of anthocyanin-rich extracts (AREs) from bilberry (Vaccinium myrtillus L.), chokeberry (Aronia meloncarpa E.), and grape (Vitis vinifera) by assessing multiple biomarkers of colon cancer in male rats treated with a colon carcinogen, azoxymethane. Fischer 344 male rats were fed the AIN-93 diet (control) or AIN-93 diet supplemented with AREs for 14 wk. Biomarkers that were evaluated included the number and multiplicity of colonic aberrant crypt foci (ACF), colonic cell proliferation, urinary levels of oxidative DNA damage, and expression of cyclooxygenase (COX) genes. To assess the bioavailability, levels of anthocyanins in serum, urine, and feces were evaluated. Total ACF were reduced (P<0.05) in bilberry, chokeberry, and grape diet groups compared with the control group. The number of large ACF was also reduced (P<0.05) in bilberry and chokeberry ARE-fed rats. Colonic cellular proliferation was decreased in rats fed bilberry ARE and chokeberry ARE diets. Rats fed bilberry and grape ARE diets had lower COX-2 mRNA expression of gene. High levels of fecal anthocyanins and increased fecal mass and fecal moisture occurred in ARE-fed rats. There was also a significant reduction (P<0.05) in fecal bile acids in ARE-fed rats. The levels of urinary 8-hydroxyguanosine were similar among rats fed different diets. These results support our previous in vitro studies suggesting a protective role of AREs in colon carcinogenesis and indicate multiple mechanisms of action.
Strathearn, Katherine E; Yousef, Gad G; Grace, Mary H; Roy, Susan L; Tambe, Mitali A; Ferruzzi, Mario G; Wu, Qing-Li; Simon, James E; Lila, Mary Ann; Rochet, Jean-Christophe
Neuropathological evidence indicates that dopaminergic cell death in Parkinson׳s disease (PD) involves impairment of mitochondrial complex I, oxidative stress, microglial activation, and the formation of Lewy bodies. Epidemiological findings suggest that the consumption of berries rich in anthocyanins and proanthocyanidins may reduce PD risk. In this study, we investigated whether extracts rich in anthocyanins, proanthocyanidins, or other polyphenols suppress the neurotoxic effects of rotenone in a primary cell culture model of PD. Dopaminergic cell death elicited by rotenone was suppressed by extracts prepared from blueberries, grape seed, hibiscus, blackcurrant, and Chinese mulberry. Extracts rich in anthocyanins and proanthocyanidins exhibited greater neuroprotective activity than extracts rich in other polyphenols, and a number of individual anthocyanins interfered with rotenone neurotoxicity. The blueberry and grape seed extracts rescued rotenone-induced defects in mitochondrial respiration in a dopaminergic cell line, and a purple basal extract attenuated nitrite release from microglial cells stimulated by lipopolysaccharide. These findings suggest that anthocyanin- and proanthocyanidin-rich botanical extracts may alleviate neurodegeneration in PD via enhancement of mitochondrial function.
Strathearn, Katherine E.; Yousef, Gad G.; Grace, Mary H.; Roy, Susan L.; Tambe, Mitali A.; Ferruzzi, Mario G.; Wu, Qing-Li; Simon, James E.; Lila, Mary Ann; Rochet, Jean-Christophe
Neuropathological evidence indicates that dopaminergic cell death in Parkinson’s disease (PD) involves impairment of mitochondrial complex I, oxidative stress, microglial activation, and the formation of Lewy bodies. Epidemiological findings suggest that the consumption of berries rich in anthocyanins and proanthocyanidins may reduce PD risk. In this study, we investigated whether extracts rich in anthocyanins, proanthocyanidins, or other polyphenols suppress the neurotoxic effects of rotenone in a primary cell culture model of PD. Dopaminergic cell death elicited by rotenone was suppressed by extracts prepared from blueberries, grape seed, hibiscus, blackcurrant, and Chinese mulberry. Extracts rich in anthocyanins and proanthocyanidins exhibited greater neuroprotective activity than extracts rich in other polyphenols, and a number of individual anthocyanins interfered with rotenone neurotoxicity. The blueberry and grape seed extracts rescued rotenone-induced defects in mitochondrial respiration in a dopaminergic cell line, and a purple basal extract attenuated nitrite release from microglial cells stimulated by lipopolysaccharide. These findings suggest that anthocyanin- and proanthocyanidin-rich botanical extracts may alleviate neurodegeneration in PD via enhancement of mitochondrial function. PMID:24502982
Wang, Sunan; Marcone, Massimo; Barbut, Shai; Lim, Loong-Tak
To modify the properties of edible soy protein isolate (SPI) films, 0.5% anthocyanin-rich red raspberry (Rubus strigosus) extract (ARRE) (0.5 g raspberry powder in 95% ethyl alcohol/water/85% lactic acid [80:19:1. v/v/v]) was incorporated into film-forming solutions. ARRE resulted in an SPI film having significantly enhanced tensile strength (P < 0.05) and % elongation at break (P < 0.05), as well as increased water swelling ratio (P < 0.05) and in vitro pepsin digestibility (P < 0.05). The resultant films also showed significantly decreased water solubility and water vapor permeability (P < 0.05). In addition, ARRE increased darkness, redness, and yellowness film appearance as evidenced by a lower L* (P < 0.05), greater positive a* (P < 0.05), and a higher b* (P < 0.05) than the control film. Scanning electron microscopy images revealed that extract-added films had denser and more compact cross-section microstructure. Fourier transform infrared spectra illustrated that ARRE-created hydrogen bonding involved conformational changes of soy protein without destroying its backbone structure. SDS-PAGE electrophoretograms revealed that the extract induced intermolecular interaction of the soy protein monomers. Natural plant extracts would be a promising ingredient to make SPI films with different physicochemical properties and applications. This study characterizes the potential physicochemical changes of SPI film with incorporated raspberry extract. Upon the above modification, the resultant film was found to enhance the applications of pure SPI film in food packaging. For example, SPI-ARRE film could prolong the usage life of SPI film due to increased strength, or could be useful as a desiccant (drying agent) such as a water-absorbing sheet for preserving dried foods due to its increased hydrophilic surface and water-swelling ratio. SPI-ARRE film could also be alternately used as a food wrap with unique color. © 2012 Institute of Food Technologists®
Takahashi, Azusa; Okazaki, Yukako; Nakamoto, Aika; Watanabe, Sanae; Sakaguchi, Hirohide; Tagashira, Yukari; Kagii, Atsuko; Nakagawara, Shunji; Higuchi, Ohki; Suzuki, Takashi; Chiji, Hideyuki
Haskap (Lonicera caerulea L.) fruit contains some bioactive phenolic phytochemicals, mainly cyanidin-3-glucoside (cy3-glc) and chlorogenic acid. The purpose of this study was to investigate the effects of anthocyanin-rich phenolic phytochemical (containing 13.2% anthocyanin) purified from a Haskap fruit (named Haskap phytochemical) on postprandial serum triglyceride and blood glucose levels. The Haskap phytochemical (containing cy 3-glc at 300 mg/kg of body weight) was administered orally to rats fasted for 24 h and 30 min later, a corn oil emulsion was administered to these rats. After the administration, serum triglyceride concentration was measured. An increase in serum triglyceride concentration and the AUC significantly lowered in the Haskap phytochemical-administered group than in the saline-administered group. To evaluate the effect of serum glucose levels, the Haskap phytochemical was orally administered to rats fasted for 24 h and sucrose solution (2 g/kg of body weight) was administered to these rats after 30 min. After the administration, blood glucose level was measured. The Haskap phytochemical significantly reduced the increase in blood glucose levels and AUC in the Haskap phytochemical-administered group than in the saline-administered group. Furthermore, to investigate the long-term effects of Haskap phytochemical intake, high-fat diet (HF diet) with 1.5% or 3.0% Haskap phytochemical was administered to rats for four weeks. The investigation of chronological changes in the serum components of the rats fed HF diets in addition to the administration of Haskap phytochemical showed that the increase in serum triglyceride concentrations, total cholesterol concentrations and blood glucose were significantly suppressed compared to the HF diet-fed control (HF-control). These results suggest that the decrease in postprandial blood lipids and blood glucose by short or long-term Haskap phytochemical ingestion is due to anthocyanin and other polyphenols
Park, Mi-Young; Kim, Jung-Mi; Kim, Jong-Sang; Choung, Myoung-Gun; Sung, Mi-Kyung
Background: Anthocyanins have been shown to inhibit cancer cell growth by suppressing oxidative stress and inflammatory responses. The purpose of this study was to investigate the effects of an anthocyanin-rich extract (AE) from black soybean coat on intestinal carcinogenesis. Methods: ApcMin/+ mice were fed a diet of 0.2% or 0.5% AE for 7 weeks. We analyzed the number of intestinal tumors, oxidative stress and inflammatory markers associated with β-catenin and cytosolic phospholipase A2 (cPLA2) signals. The number of intestinal tumors, and cellular expression of β-catenin were determined. Results: The number of intestinal tumors was significantly lower in mice fed a 0.5% AE diet compared to those of the other groups. Cytosolic β-catenin expression was significantly decreased in the AE supplemented groups compared to that of the control animals. In addition, mucosa expression of cyclooxygenase-2 and cPLA2 were also significantly decreased in the 0.5% AE group, by 32% and 62%, respectively, compared to the control group. Conclusions: These results suggest that dietary AE reduced the development of intestinal tumors, possibly through the ability to suppress oxidative stresses, decreasing inflammatory responses mediated by β-catenin associated signals. PMID:26473158
The protective effects of anthocyanin-rich blueberries on brain health are well documented and are particularly important under conditions of high oxidative stress which can lead to “accelerated aging”. One such scenario is exposure to space radiation, which consists of high-energy and -charge parti...
Wallace, Taylor C; Giusti, M Monica
Cacao (Theobroma cacao L.) is rich in procyanidins, a large portion of which degrades during the natural fermentation process of producing cocoa powder. Recent advances in technology have enabled scientists to produce unfermented cocoa powder, preserving the original profile of procyanidins present in cocoa and allowing for the development of highly concentrated procyanidin-rich extracts. During this process, the anthocyanins naturally present in unfermented cocoa remain intact, producing a violet color in the final extract. The objective of this study was to selectively remove the violet color in procyanidin-rich extracts produced from unfermented cocoa powder, while maintaining the stability and composition of procyanidins present in the matrix. Several processing parameters, including pH fluctuations, enzymatic treatments, and the addition of potassium meta-bisulfite, were explored to influence the color of procyanidin-rich extracts throughout a 60-d shelf life study. The addition of potassium meta-bisulfite (500 ppm) was found to be the most effective means of removing the violet color present in the treated extracts (L*= 71.39, a*= 8.44, b*= 9.61, chroma = 12.79, and hue = 48.8˚) as compared to the control (L*= 52.84, a*= 11.08, b*= 2.24, chroma = 11.28, and hue = 11.4˚). The use of potassium meta-bisulfite at all treatment levels (200, 500, and 1000 ppm) did not show any significant detrimental effects on the stability, composition, or amount of procyanidins present in the extracts over the shelf life period as monitored by UV-Vis spectrophotometry and HPLC-MS. This research will enable the food industry to incorporate highly concentrated procyanidin-rich extracts in food products without influencing the color of the final product. © 2011 Institute of Food Technologists®
Joshi, Robin; Rana, Ajay; Gulati, Ashu
Recently anthocyanin-rich purple tea varieties have been developed. The quality of these new purple tea varieties developed in Kangra valley was assessed, and compared with the quality of tea from standard Kangra clone. Purple tea shoots (PL) recorded higher amount of polyphenols compared to standard green tea shoot (GL) while epigallocatechin gallate (EGCG) recorded higher levels in GL. Higher levels of theaflavins were recorded in orthodox black tea from purple shoots (BTP) compared to black tea (BT) made from green shoots. Both theanine and caffeine recorded higher levels in GL. Volatile flavour profiles of these teas showed qualitative and quantitative differences. Aroma extract dilution assay showed higher dilution factors in BTP than BT. Orthodox teas from purple shoots exhibited higher antioxidant activity compared to standard black tea. Strong correlation of total quality scores with aroma and infusion colour was observed. Tea from anthocyanin-rich cultivars can become specialty teas with high antioxidant activity.
Black beans contain anthocyanins that could be used as colorants in foods with associated health benefits. The objective was to optimize anthocyanins extraction from black bean coats and evaluate their physicochemical stability and antidiabetes potential. Optimal extraction conditions were 24% ethan...
Sui, Xiaonan; Zhang, Yan; Zhou, Weibiao
Anthocyanin-rich black rice extract powder (ABREP) as a nutraceutical source was fortified into bread. The quality and digestibility behaviors of bread with ABREP were evaluated through instrumental and in vitro digestion studies. The quality of bread with 2% of ABREP was not significantly (p>0.05) different from the control bread; however, increasing the ABREP level to 4% caused less elasticity and higher density of bread. A mathematical model was further developed to systemically describe the trajectory of bread digestion. The digestion rates of bread with ABREP were found to be reduced by 12.8%, 14.1%, and 20.5% for bread with 1%, 2%, and 4% of ABREP, respectively. Results of the study suggest that the fortification of anthocyanins into bread could be an alternative way to produce functional bread with a lower digestion rate and extra health benefits. Copyright © 2015 Elsevier Ltd. All rights reserved.
Jing, P; Giusti, M M
Purple corn (Zea mays L.) is a rich and economic source of anthocyanin colorants and functional ingredients. However, high levels of anthocyanin-rich waste are generated during processing, reducing the yields and increasing the costs of the final product. This waste has been associated with anthocyanin complexation with tannins and proteins. Our objective was to evaluate anthocyanin extraction methods to reduce purple corn waste. Different solvents (water, 0.01%-HCl-acidified water, and 0.01%-HCl-acidified ethanol), temperatures (room temperature, 50, 75, and 100 degrees C), and times of exposure to the solvents were investigated. Acetone (70% acetone in water) extraction was used as control. Anthocyanins, total phenolics, tannins, and proteins in extracts were measured by the pH differential, Folin-Ciocalteu, protein precipitation, and BCA assay methods. Qualitative analyses were done by HPLC coupled to a PDA detector and SDS-PAGE analysis. Water at 50 degrees C achieved the highest yield of anthocyanins (0.94 +/- 0.03 g per 100 g dry corncob) with relatively low tannins and proteins, comparable to the anthocyanin yield obtained by 70% acetone (0.98 +/- 0.08 g per 100 g dry corncob). Extending the extraction time from 20 to 60 min and using consecutive reextraction procedures reduced anthocyanin purity, increasing the yields of other phenolics. A neutral protease was applied to the extracts and effectively decomposed the major protein that was believed to contribute to the development of anthocyanin complexation and waste generation. Extraction time, consecutive reextraction procedures, and enzyme hydrolysis should be considered for high yield of anthocyanins and waste reduction.
Kang, Min-Kyung; Lim, Soon Sung; Lee, Jae-Yong; Yeo, Kyung Mok; Kang, Young-Hee
Diabetic nephropathy (DN) is one of the major diabetic complications and the leading cause of end-stage renal disease. Abnormal angiogenesis results in new vessels that are often immature and play a pathological role in DN, contributing to renal fibrosis and disrupting glomerular failure. Purple corn has been utilized as a daily food and exerts disease-preventive activities. This study was designed to investigate whether anthocyanin-rich purple corn extract (PCE) prevented glomerular angiogenesis under hyperglycemic conditions. Human endothelial cells were cultured in conditioned media of mesangial cells exposed to 33 mM high glucose (HG-HRMC-CM). PCE decreased endothelial expression of vascular endothelial growth factor (VEGF) and hypoxia inducible factor (HIF)-1α induced by HG-HRMC-CM. Additionally, PCE attenuated the induction of the endothelial marker of platelet endothelial cell adhesion molecule (PECAM)-1 and integrin β3 enhanced in HG-HRMC-CM. Endothelial tube formation promoted by HG-HRMC-CM was disrupted in the presence of PCE. In the in vivo study employing db/db mice treated with 10 mg/kg PCE for 8 weeks, PCE alleviated glomerular angiogenesis of diabetic kidneys by attenuating the induction of VEGF and HIF-1α. Oral administration of PCE retarded the endothelial proliferation in db/db mouse kidneys, evidenced by its inhibition of the induction of vascular endothelium-cadherin, PECAM-1 and Ki-67. PCE diminished the mesangial and endothelial induction of angiopoietin (Angpt) proteins under hypeglycemic conditions. The induction and activation of VEGF receptor 2 (VEGFR2) were dampened by treating PCE to db/db mice. These results demonstrate that PCE antagonized glomerular angiogenesis due to chronic hyperglycemia and diabetes through disturbing the Angpt-Tie-2 ligand-receptor system linked to renal VEGFR2 signaling pathway. Therefore, PCE may be a potent therapeutic agent targeting abnormal angiogenesis in DN leading to kidney failure. PMID:24278186
Taheri, Rod; Connolly, Bryan A; Brand, Mark H; Bolling, Bradley W
Polyphenols from underutilized black, purple, and red aronia (Aronia melanocarpa, Aronia prunifolia, and Aronia arbutifolia) and 'Viking' (Aronia mitschurinii) berries were characterized. Anthocyanin and nonanthocyanin flavonoids were quantitated by UHPLC-DAD-MS and proanthocyanidins by normal-phase HPLC. On a dry weight basis, anthocyanins were mainly cyanidin-3-galactoside, highest in black aronia (3.4-14.8 mg/g) and lowest in red aronia (0.5-0.8 mg/g) as cyandin-3-galactoside equivalents. Berries from 'Viking' and the red accession UC021 had substantially more proanthocyanidins than the other accessions, with 3.3 and 3.8 mg catechin equiv/g, respectively. Chlorogenic acids and quercetin glycosides were most abundant in purple UC047 berries, at 17.3 and 1.3 mg/g, respectively. In contrast to anthocyanin content, total phenol values were highest in berries from red and purple accessions and attributed to phenolic acid and proanthocyanin content. Thus, red, purple, and black aronia berries are rich sources of polyphenols with various levels of polyphenol classes.
Kalušević, Ana; Lević, Steva; Čalija, Bojan; Pantić, Milena; Belović, Miona; Pavlović, Vladimir; Bugarski, Branko; Milić, Jela; Žilić, Slađana; Nedović, Viktor
Black soybean coat is insufficiently valorised food production waste rich in anthocyanins. The goal of the study was to examine physicochemical properties of spray dried extract of black soybean coat in regard to carrier materials: maltodextrin, gum Arabic, and skimmed milk powder. Maltodextrin and gum Arabic-based microparticles were spherical and non-porous while skimmed milk powder-based were irregularly shaped. Low water activity of microparticles (0.31-0.33), good powders characteristics, high solubility (80.3-94.3%) and encapsulation yields (63.7-77.0%) were determined. All microparticles exhibited significant antioxidant capacity (243-386 μmolTE/g), good colour stability after three months of storage and antimicrobial activity. High content of total anthocyanins, with cyanidin-3-glucoside as predominant, were achieved. In vitro release of anthocyanins from microparticles was sustained, particularly from gum Arabic-based. These findings suggest that proposed simple eco-friendly extraction and microencapsulation procedures could serve as valuable tools for valorisation and conversion of black soybean coat into highly functional and stable food colourant.
Silva, S; Costa, E M; Mendes, M; Morais, R M; Calhau, C; Pintado, M M
The present work aimed to characterize the impact of an anthocyanin-rich blueberry extract upon the growth, adhesion and biofilm formation of several pathogens including some multiresistant bacteria. A group comprised of reference strains and clinical multiresistant isolates of Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Acinetobacter baumannii and Staphylococcus aureus, were used to screen for antimicrobial activity. Microbial growth was determined through the measurement of the optical density while adhesion and biofilm formation was determined using the standard crystal violet staining procedure. The results showed that, while blueberry extract was only effective in hindering the growth of Staph. aureus and E. coli, it was capable of significantly inhibiting biofilm formation and bacterial adhesion for all micro-organisms tested. The extract demonstrated a considerable potential as a natural, alternative antimicrobial capable of either interfering with microbial growth or hamper the adhesion to surfaces, with Staph. aureus proving to be the most susceptible micro-organism. The overall study demonstrates the potential of anthocyanin extracts as natural effective alternative antimicrobial agents. Additionally, the extract's capacity to reduce adhesion without reducing bacterial growth reduces the likeliness of resistance development while reducing the probability of infection. © 2016 The Society for Applied Microbiology.
Sonoda, Keisuke; Aoi, Wataru; Iwata, Tomoaki; Li, Yanmei
Specific anthocyanin-rich dietary factors have been shown to improve metabolic functions associated with thermogenesis in animal studies. Aronia melanocarpa, commonly known as wild chokeberry, contains a high level of anthocyanin that would be expected to maintain body temperature through thermogenesis. We here investigated the effects of Aronia melanocarpa extracts on body temperature and peripheral blood flow in healthy women with a cold constitution. A pre/post comparison trial was performed in 11 women with a cold constitution, who were taking Aronia melanocarpa extracts (150 mg/day) for 4 weeks. Physiological and biochemical parameters, along with psychological tests were examined. The subjects' body surface temperature was significantly higher in the post-trial than in the pre-trial. In psychological tests, factors related to cold were significantly improved by Aronia intake. On the other hand, peripheral blood flow was not affected by Aronia supplementation. Plasma noradrenalin level was significantly elevated by Aronia intake, and subjects with a higher level of 8-hydroxy-2'-deoxyguanosine in the pre-trial showed decreased levels in the post-trial. These data suggest that dietary Aronia melanocarpa extract improves the maintenance of body temperature in healthy women with a cold constitution, which may be mediated by noradrenalin and oxidative stress levels.
Li, Haibo; Zhu, Lixia; Yuan, Gaigai; Heng, Shuangping; Yi, Bin; Ma, Chaozhi; Shen, Jinxiong; Tu, Jinxing; Fu, Tingdong; Wen, Jing
Because of the advantages of anthocyanins, the genetics and breeding of crops rich in anthocyanins has become a hot research topic. However, due to the lack of anthocyanin-related mutants, no regulatory genes have been mapped in Brassica napus. In this study, we first report the characterization of a B. napus line with purple leaves and the fine mapping and candidate screening of the BnaA.PL1 gene. The amount of anthocyanins in the purple leaf line was six times higher than that in a green leaf line. A genetic analysis indicated that the purple character was controlled by an incomplete dominant gene. Through map-based cloning, we localized the BnaA.PL1 gene to a 99-kb region at the end of B. napus chromosome A03. Transcriptional analysis of 11 genes located in the target region revealed that the expression level of only the BnAPR2 gene in seedling leaves decreased from purple to reddish green to green individuals, a finding that was consistent with the measured anthocyanin accumulation levels. Molecular cloning and sequence analysis of BnAPR2 showed that the purple individual-derived allele contained 17 variants. Markers co-segregating with BnaA.PL1 were developed from the sequence of BnAPR2 and were validated in the BC4P2 population. These results suggested that BnAPR2, which encodes adenosine 5'-phosphosulfate reductase, is likely to be a valuable candidate gene. This work may lay the foundation for the marker-assisted selection of B. napus vegetables that are rich in anthocyanins and for an improved understanding of the molecular mechanisms controlling anthocyanin accumulation in Brassica.
Guo, Honghui; Ling, Wenhua; Wang, Qing; Liu, Chi; Hu, Yan; Xia, Min; Feng, Xiang; Xia, Xiaodong
This study was designed to evaluate the effect of an anthocyanin-rich extract from black rice on hyperlipidemia and insulin resistance in fructose-fed rats. Rats fed fructose diet for 4 weeks exhibited significantly higher plasma insulin levels and lower insulin sensitivity than the control rats fed AIN-93G diet. Dietary supplementation with the anthocyanin-rich extract (5 g/kg of high-fructose diet) prevented the development of fructose-induced insulin resistance. After fructose-induced insulin resistance had been established, 4-week treatment with the anthocyanin-rich extract (5 g/kg of high-fructose diet) or pioglitazone (270 mg/kg of high-fructose diet) ameliorated the glucose intolerance and hyperlipidemia, but the extract failed to reverse the fructose-induced hyperinsulinemia as pioglitazone did. In addition, rats supplemented by the extract exhibited lower oxidative stress than the fructose-fed controls, as indicated by the lower concentrations of plasma thiobarbituric acid reactive substances and blood oxidized glutathione. Overall, these results suggest that the anthocyanin-rich extract from black rice improves certain metabolic abnormalities associated with diets high in fructose.
The protective effects of anthocyanin-rich blueberries (BB) on brain health are well documented and are particularly important under conditions of high oxidative stress, which can lead to “accelerated aging.” One such scenario is exposure to space radiation, consisting of high-energy and -charge par...
Krenn, L; Steitz, M; Schlicht, C; Kurth, H; Gaedcke, F
The fundamental nutritional benefit of fruit and vegetables in the prevention of degenerative diseases--especially in the light of the current "anti-aging wave"--has directed the attention of scientists and consumers to a variety of berry fruits and their constituents. Many of these fruits, e.g. blueberries, elderberries or cranberries, have a long tradition in European and North American folk medicine. Based on these experiences and due to the growing interest the number of food supplements on the market containing fruit powders, juice concentrates or extracts of these fruits has increased considerably. Advertising for these products mainly focusses on the phenolic compounds, especially the anthocyanins and proanthocyanidins and their preventive effects. Most of the preparations are combinations, e.g. of extracts of different fruits with vitamins and trace elements, etc. which are labelled in a way which does not allow a comparison of the products. Typically, information on the extraction solvent, the drug: extract ratio and the content of anthocyanins and proanthocyanidins is missing. Besides that, the analysis of these polyphenols causes additional problems. Whereas the quality control of herbal medicinal products is regulated in detail, no uniform requirements for food supplements are existing. A broad spectrum of methods is used for the assay of the constituents, leading to differing, incomparable results. In addition to that, the methods are quite interference-prone and consequently lead to over- or underestimation of the contents. This publication provides an overview of some selected berries (lingonberry, cranberry, black elderberry, black chokeberry, black currant, blueberry), their constituents and use. The analytical methods currently used for the identification and quantification of the polyphenols in these berries are described, including an evaluation of their advantages and disadvantages.
Su, Nana; Wu, Qi; Liu, Yuanyuan; Cai, Jiangtao; Shen, Wenbiao; Xia, Kai; Cui, Jin
The aims of the study were to investigate whether hydrogen gas (H2) was involved in regulation of anthocyanin biosynthesis in two contrasting radish (Raphanus sativus L.) varieties (low [LA] and high [HA] level of anthocyanin) under UV irradiation. The results showed that hydrogen-rich water (HRW) significantly blocked the UV-A-induced increase of H2O2 and O2(•-) accumulation, and enhanced the UV-A-induced increase of superoxide dismutase (SOD) and ascorbate peroxidase (APX) activities in LA and HA. Furthermore, UV-A-induced increase of anthocyanin and total phenols was further enhanced only in HA sprouts cotreated with HRW. LC-MS/MS analysis showed that five anthocyanidins existed in HA sprouts, but only two in LA sprouts. Meanwhile, the cyanidin was the most abundant anthocyanidin in HA, and the cyanidin was 2-fold higher cotreated with HRW than UV-A. Molecular analyses showed that the anthocyanin biosynthesis-related genes were upregulated significantly in both HA (in particular) and LA sprouts treated with HRW plus UV-A. These data imply that HRW reestablishes reactive oxygen species homeostasis in both LA and HA, but exerts different effects on anthocyanin accumulation between them under UV-A.
Ozkol, Hatice Uce; Koyuncu, Ismail; Tuluce, Yasin; Dilsiz, Nihat; Soral, Sinan; Ozkol, Halil
Ultraviolet radiation (UV) was reported to cause oxidative stress. Hibiscus sabdariffa L. (Malvaceae) calyx is commonly used in traditional Asian and African medicines and possesses strong antioxidant capacity due to its anthocyanin (ANTH) content. This study researched the possible protective role of Hibiscus sabdariffa calyx extract (HSCE) in UVC exposure of rats. Levels of serum enzymes, renal function tests, and some oxidant/antioxidant biomarkers of skin, lens, and retina tissues were monitored. Rats were exposed to UVC 4 h daily for 40 d and simultaneously received HSCE containing 2.5, 5, and 10 mg doses of ANTH in drinking water. Significant (p < 0.05) increases in the levels of serum aminotransferases, lactate dehydrogenase, urea, creatinine, and uric acid were noted after UVC exposure. In skin, lens, and retina tissues, total oxidant status, oxidative stress index, lipid peroxidation, and protein oxidation escalated markedly (p < 0.05) whereas total antioxidant status, reduced glutathione, and superoxide dismutase decreased dramatically (p < 0.05) related to UVC. Co-administration of HSCE with each ANTH dose significantly (p < 0.05) reversed aforementioned parameters (except total oxidant status) almost in all tissues. The LD50 of HSCE in rats was determined to be above 5000 mg/kg. Our data revealed that HSCE has a remarkable potential to counteract UVC-caused impairments, probably through its antioxidant and free radical-defusing effects. Therefore, HSCE could be useful against some cutaneous and ocular diseases in which UV and oxidative stress have a role in the etiopathogenesis.
Han, Kyu-Ho; Matsumoto, Asami; Shimada, Ken-ichiro; Sekikawa, Mitsuo; Fukushima, Michihiro
We examined the antioxidant effects of polyphenol/anthocyanin-rich potato (Solanum tuberosum cv. Shadow-Queen) flakes in male rats fed a high-cholesterol diet. The rats were served either a high-cholesterol (0.5% cholesterol plus 0.125% sodium cholate) diet, or a high-cholesterol diet containing a mixture of 243 g alpha-maize starch/kg supplemented with one of the following (per kg diet): 300 g medium purple potato (Shadow-Queen), 300 g white potato (Solanum tuberosum cv. Toyoshiro) or 300 g dark purple sweet potato (Ipomoea batatas cv. Ayamurasaki) flakes for 28 d. We analysed thiobarbituric acid reactive substance (TBARS) levels in the serum and liver, and antioxidant enzyme activities in the liver. At this dosage, TBARS levels in the serum and liver of the Shadow-Queen and Ayamurasaki groups were significantly lower than those in the control and Toyoshiro groups. The serum urate levels in all the flake groups were significantly lower than that in the control group. The hepatic glutathione levels in the Shadow-Queen and Ayamurasaki groups were significantly higher than in the control and Toyoshiro groups. The activities of hepatic glutathione reductase and glutathione S-transferase in the Shadow-Queen and Ayamurasaki groups were significantly greater than those in the control group. These results show that modulation of antioxidant enzymes and oxidative status in the serum and liver by the purple potato flake diet (Shadow-Queen) containing polyphenols/anthocyanins may play an important role in the protection against adverse effects related to oxidative damage in rats fed a high-cholesterol diet.
Chang, Yun-Ching; Huang, Kai-Xun; Huang, An-Chung; Ho, Yung-Chyuan; Wang, Chau-Jong
The oxidative modification of low-density lipoprotein (LDL) plays a key role in the pathogenesis of atherosclerosis. Anti-oxidative reagents, which can effectively inhibit LDL oxidation, may prevent atherosclerosis via reducing early atherogenesis, and slowing down the progression to advance stages. As shown in previous studies Hibiscus sabdariffa L. is a natural plant containing a lot of pigments that was found to possess anti-oxidative of activity. Therefore, in this study, we evaluated the anti-oxidative activity of Hibiscus anthocyanins (HAs) by measuring their effects on LDL oxidation (in cell-free system) and anti-apoptotic abilities (in RAW264.7 cells). HAs have been tested in vitro examining their relative electrophoretic mobility (REM), Apo B fragmentation, thiobarbituric acid relative substances (TBARS) and radical 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging activity assay. The anti-oxidative activity of HAs was defined by relative electrophoretic mobility of oxLDL (decrease of 50% at 2 mg/ml), fragmentation of Apo B (inhibition of 61% at 1mg/ml), and TBARS assay (IC(50): 0.46 mg/ml) in the Cu(2+)-mediated oxidize LDL. Furthermore, the addition of >0.1 mg/ml of HAs could scavenge over 95% of free DPPH radicals, HAs showed strong potential in inhibiting LDL oxidation induced by copper. In addition, to determine whether oxLDL-induced apoptosis in macrophages is inhibited by HAs, we studied the viability, morphology and caspase-3 expression of RAW 264.7 cells. MTT assay, Leukostate staining analysis and Western blotting reveals that HAs could inhibit oxLDL-induced apoptosis. According to these findings, we suggest that HAs may be used to inhibit LDL oxidation and oxLDL-mediated macrophage apoptosis, serving as a chemopreventive agent. However, further investigations into the specificity and mechanism(s) of HAs are needed.
Zapolska-Downar, Danuta; Nowicka, Grazyna; Sygitowicz, Grazyna; Jarosz, Mirosław
It has been previously reported that dietary polyphenolic compounds have a positive effect in cardiovascular diseases, although the underlying mechanisms remain unknown. In this study, the effects of Aronox, an anthocyanin-rich extract from Aronia melanocarpa E, on human umbilical vein endothelial cell (HUVEC) apoptosis was investigated. Apoptosis was measured in HUVEC pretreated with Aronox and than treated with 7beta-hydroxycholesterol (20 microg/ml). For the evaluation of apoptosis we used the cell binding of annexin V, the propidium iodide uptake method and the TUNEL assay. We also measured the generation of reactive oxygen species (ROS) in the cells, using fluorescent probe 2',7'-dichlorofluorescein acetate. Moreover, alteration of the mitochondrial membrane potential with subsequent cytochrome c release, activation of caspase-3, and the level of anti-apoptotic Bcl-2 were investigated. Aronox significantly decreased 7beta-hydroxycholesterol-induced apoptosis and ROS generation, and ameliorated the collapse of the mitochondrial transmembrane potential with subsequent inhibition of cytochrome c release. Furthermore, down-regulation of Bcl-2 and up-regulation of caspase-3 activation were reversed by Aronox. The protective action of the extract against apoptosis in endothelial cells may contribute to the potential benefits drawn from consumption of plant polyphenols. Copyright 2009 S. Karger AG, Basel.
Mauray, A; Felgines, C; Morand, C; Mazur, A; Scalbert, A; Milenkovic, D
Intake of anthocyanin-rich foods has been associated with a reduced risk of cardiovascular diseases. We recently reported that a nutritional supplementation with a bilberry anthocyanin-rich extract (BE) attenuates atherosclerotic lesion development in apolipoprotein E-deficient (apoE⁻/⁻) mice. However, the mechanism(s) of their preventive action are not completely understood. Anthocyanins may alter mRNA levels of genes related to atherosclerosis in cultured macrophages and endothelial cells, but in vivo studies remain scarce. The aim of the present study was to explore the in vivo mechanisms of action of the same bilberry extract, administered by supplementation at a nutritional level, in the aorta of apo E⁻/⁻ mice using a global transcriptomic approach. This study focused on the early stage of atherosclerosis development for better assessment of BE action on initiation mechanisms of this pathology. After a two week period, plasma lipid and antioxidant capacity were evaluated and the global genomic analysis was carried out using pangenomic microarrays. BE supplementation significantly improved hypercholesterolemia whereas the plasmatic antioxidant status remained unchanged. Nutrigenomic analysis identified 1261 genes which expression was modulated by BE in the aorta. Bioinformatic analysis revealed that these genes are implicated in different cellular processes such as oxidative stress, inflammation, transendothelial migration and angiogenesis, processes associated with atherosclerosis development/protection. Some of the most significantly down-regulated genes included genes coding for AOX1, CYP2E1 or TXNIP implicated in the regulation of oxidative stress, JAM-A coding for adhesion molecules or VEGFR2 implicate in regulation of angiogenesis. Other genes were up-regulated, such as CRB3, CLDN14 or CDH4 potentially associated with increased cell-cell adhesion and decreased paracellular permeability. These results provide a global integrated view of the
Sarkar, Biswatrish; Kumar, Dhananjay; Sasmal, Dinakar; Mukhopadhyay, Kunal
Anthocyanin extracts (AEs) from Ocimum tenuiflorum (leaf), Hibiscus rosa-sinensis (petal) and Hibiscus sabdariffa (calyx) were investigated and compared for in vitro antioxidant activity and DNA damage protective property. Total phenolic content (TPC) and total anthocyanin content (TAC) of the AEs were determined and the major anthocyanins were characterised. In vitro antioxidant activities were assessed by ferric-reducing antioxidant power (FRAP) assay, 2,2-diphenyl-1-picryl hydrazyl (DPPH) radical-scavenging activity, 2-deoxy-D-ribose degradation assay and lipid peroxidation assay. The protective property of the AEs was also examined against oxidative DNA damage by H2O2 and UV using pUC19 plasmid. All the AEs particularly those from O. tenuiflorum demonstrated efficient antioxidant activity and protected DNA from damage. Strong correlation between antioxidant capacity and TPC and TAC was observed. Significant correlation between antioxidant capacity and TPC and TAC ascertained that phenolics and anthocyanins were the major contributors of antioxidant activity.
Mertens-Talcott, Susanne U; Rios, Jolian; Jilma-Stohlawetz, Petra; Pacheco-Palencia, Lisbeth A; Meibohm, Bernd; Talcott, Stephen T; Derendorf, Hartmut
The acai berry is the fruit of the acai palm and is traditionally consumed in Brazil but has gained popularity abroad as a food and functional ingredient, yet little information exists on its health effect in humans. This study was performed as an acute four-way crossover clinical trial with acai pulp and clarified acai juice compared to applesauce and a non-antioxidant beverage as controls. Healthy volunteers (12) were dosed at 7 mL/kg of body weight after a washout phase and overnight fast, and plasma was repeatedly sampled over 12 h and urine over 24 h after consumption. Noncompartmental pharmacokinetic analysis of total anthocyanins quantified as cyanidin-3-O-glucoside showed Cmax values of 2321 and 1138 ng/L at t max times of 2.2 and 2.0 h, and AUC last values of 8568 and 3314 ng h L(-1) for pulp and juice, respectively. Nonlinear mixed effect modeling identified dose volume as a significant predictor of relative oral bioavailability in a negative nonlinear relationship for acai pulp and juice. Plasma antioxidant capacity was significantly increased by the acai pulp and applesauce. Individual increases in plasma antioxidant capacity of up to 2.3- and 3-fold for acai juice and pulp, respectively were observed. The antioxidant capacity in urine, generation of reactive oxygen species, and uric acid concentrations in plasma were not significantly altered by the treatments. Results demonstrate the absorption and antioxidant effects of anthocyanins in acai in plasma in an acute human consumption trial.
Marpaung, Abdullah Muzi; Andarwulan, Nuri; Hariyadi, Purwiyatno; Nur Faridah, Didah
A spectroscopic study was conducted to evaluate the colour degradation mechanism of anthocyanin-rich extract from butterfly pea petal. The extract was diluted in four different solvent systems, which were buffer solution pH 7 (AQ7) and the mixture of organic solvent with buffer solution pH 7 (4:1 v/v). The organic cosolvent involved were methanol (ME7), ethanol (ET7) and acetone (AC7). The samples were stored in containers with 0% and 50% headspace, and their colour intensity, total anthocyanin and hypsochromic shift were evaluated periodically. The rank of colour and anthocyanin degradation from the biggest was AQ7 > ME7 > ET7 > AC7. The longest hypsochromic shift was AQ7 > ME7 > ET7, while in AC7 the shift was absent. There was evidence that the volume of package headspace provoked colour stability. The colour degradation in AC7 was proposed to occur through hydrophobic interaction unfolding, and in AQ7 was through the deacylation, while in ME7 and ET7 was due to both mechanisms.
Lee, Ja-Yeon; Im, Young-Kum; Ko, Hyun-Mi; Chin, Jong-Eon; Kim, Il-Chul; Lee, Hwanghee Blaise; Bai, Suk
To produce an alcoholic beverage containing anthocyanins that can act as antioxidants and have anticarcinogenic activities and antihypertensive effects. High starch-assimilating sake yeast strain of Saccharomyces cerevisiae co-expressing the glucoamylase and α-amylase genes from Debaryomyces occidentalis using the double rDNA-integration system was developed. The new strain grew substantially using 5 % (w/v) purple sweet potato flour as the sole carbon source. Its cell yield reached 14.5 mg ml(-1) after 3 days. This value was 2.4-fold higher than that of the parental wild-type strain. It produced 12 % (v/v) ethanol from 20 % (w/v) purple sweet potato flour and consumed 98 % of the starch content in purple sweet potato flour after 5 days of fermentation. We have produced a health-promoting alcoholic beverage abundant in anthocyanins from purple sweet potato.
Tsai, Tsung-Chang; Huang, Hui-Pei; Chang, Yun-Ching; Wang, Chau-Jong
A previous study reported that anthocyanins from roselle (Hibiscus sabdariffa L.) showed significant anticancer activity in human promyelocytic leukemia cells. To explore the antitumor effect of anthocyanin, a roselle bioactive polyphenol in a rat model of chemical-induced leukemia was assayed. Anthocyanin extract of roselle (Hibiscus anthocyanins, HAs) was supplemented in the diet (0.1 and 0.2%). This study was carried out to evaluate the protective effect of HAs on N-nitrosomethylurea (NMU)-induced leukemia of rats. The study employed male Sprague-Dawley rats (n = 48), and leukemia was induced by intravenous injection of 35 mg kg(-1) body weight of NMU dissolved in physiologic saline solution. The rats were divided into four groups (n = 12): control, NMU only, and HAs groups that received different doses of HAs (0.1 and 0.2%) daily, orally, after NMU injection. After 220 days, the animals were killed, and the following parameters were assessed: morphological observation, hematology examination, histopathological assessment, and biochemical assay. When compared with the NMU-only group, HAs significantly prevented loss of organ weight and ameliorated the impairment of morphology, hematology, and histopathology. Treatment with HAs caused reduction in the levels of AST, ALT, uric acid, and MPO. Also, the results showed that oral administration of HAs (0.2%) remarkably inhibited progression of NMU-induced leukemia by approximately 33.3% in rats. This is the first report to demonstrate that the sequential administration of HAs followed by NMU resulted in an antileukemic activity in vivo.
Lago, Chiara; Landoni, Michela; Cassani, Elena; Cantaluppi, Enrico; Doria, Enrico; Nielsen, Erik; Giorgi, Annamaria; Pilu, Roberto
In the second half of the last century, the American dent hybrids began to be widely grown, leading to the disappearance or marginalization of the less productive traditional varieties. Nowadays the characterization of traditional landraces can help breeders to discover precious alleles that could be useful for modern genetic improvement and allow a correct conservation of these open pollinated varieties (opvs). In this work we characterized the ancient coloured cultivar “Millo Corvo” typical of the Spanish region of Galicia. We showed that this cultivar accumulates high amounts of anthocyanins (83.4 mg/100g flour), and by TLC (Thin Layer Chromatography) and HPLC (High Pressure Liquid Chromatography) analysis, we demonstrated that they mainly consisted of cyanidin. Mapping and sequencing data demonstrate that anthocyanin pigmentation is due to the presence of the red color1 gene(r1), a transcription factor driving the accumulation of this pigment in the aleurone layer. Further chemical analysis showed that the kernels are lacking in carotenoids, as confirmed by genetic study. Finally a DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging ability test showed that Millo Corvo, even though lacking carotenoids, has a high antioxidant ability, and could be considered as a functional food due to the presence of anthocyanins. PMID:25961304
Lago, Chiara; Landoni, Michela; Cassani, Elena; Cantaluppi, Enrico; Doria, Enrico; Nielsen, Erik; Giorgi, Annamaria; Pilu, Roberto
In the second half of the last century, the American dent hybrids began to be widely grown, leading to the disappearance or marginalization of the less productive traditional varieties. Nowadays the characterization of traditional landraces can help breeders to discover precious alleles that could be useful for modern genetic improvement and allow a correct conservation of these open pollinated varieties (opvs). In this work we characterized the ancient coloured cultivar "Millo Corvo" typical of the Spanish region of Galicia. We showed that this cultivar accumulates high amounts of anthocyanins (83.4 mg/100g flour), and by TLC (Thin Layer Chromatography) and HPLC (High Pressure Liquid Chromatography) analysis, we demonstrated that they mainly consisted of cyanidin. Mapping and sequencing data demonstrate that anthocyanin pigmentation is due to the presence of the red color1 gene(r1), a transcription factor driving the accumulation of this pigment in the aleurone layer. Further chemical analysis showed that the kernels are lacking in carotenoids, as confirmed by genetic study. Finally a DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging ability test showed that Millo Corvo, even though lacking carotenoids, has a high antioxidant ability, and could be considered as a functional food due to the presence of anthocyanins.
Jurgoński, Adam; Juśkiewicz, Jerzy; Zduńczyk, Zenon
The berries of blue honeysuckle (Lonicera caerulea L.), including an edible Kamchatka variety (var. kamtschatica Sevast.), are a potential but relatively unknown source of anthocyanins, which are thought to have favorable effects on diabetes and cardiovascular disease (CVD). The aim of this study was to examine whether the dietary addition of a Kamchatka honeysuckle berry extract (KHBE, 327 mg anthocyanins/g) is able to limit the disorders related to these diseases induced by a high-fructose diet in rats. The experiment was conducted using 24 adult male Wistar rats distributed into 3 groups of 8 animals each and fed semipurified casein diets differentiated by the carbohydrate source for 4 wk, as follows: a control cornstarch diet (681 g/kg) or a high-fructose diet (633 g/kg), with or without the addition of KHBE (2 g/kg). The mucosal lactase activity in the small intestine was increased in the rats fed the KHBE-containing diet compared with the rats fed the control diet. In the cecal digesta, the dietary KHBE considerably increased bacterial α- and β-glucosidase activity. Furthermore, hyperlipidemia, hyperinsulinemia, insulin resistance, and impaired glucose tolerance were detected in the rats fed the high-fructose diet. The dietary KHBE normalized the plasma triglyceride concentration and atherogenicity, whereas plasma non-HDL cholesterol, insulin concentration, and insulin resistance were ameliorated to levels comparable with the rats fed the control diet. An anthocyanin-rich Kamchatka honeysuckle berry extract supplemented to an unbalanced diet is able to ameliorate the disturbances in lipid and glucose metabolism that are the fundamental risk factors for CVD and diabetes. Moreover, the extract stimulates enzymatic activity within the gut that seems to be related to the metabolism of polyphenols. Copyright © 2013 Elsevier Inc. All rights reserved.
Gao, Ruichang; Jing, Pu; Ruan, Siyu; Zhang, Yifan; Zhao, Shujuan; Cai, Zhan; Qian, Bingjun
In this paper, we examined the role of chitosan in the removal of off-flavours from radish anthocyanin-rich pigments and studied the mechanisms of the process. Four radish glucosinolates (glucoraphenin, dehydroerucin, glucobrassicin, and glucoerucin) were identified by LC-MSn from root extracts and dehydroerucin was found to be the major glucosinolate in red radish roots. Application of chitosan with 76%, 83% or 89% deacetylation in radish extracts attributed to 26%, 35% or 43% adsorption rate for glucosinolates, and 28%, 26% or 22% for anthocyanins, respectively. HS-SPME/GC-MS analysis demonstrated that the concentration of volatile compounds decreased by 70%, resulting in the loss of odorous compounds. The changes in chitosan spectra before/after adsorption and after desorption at 1590 and 3360cm(-1) and at broad bands from 2600 to 2000cm(-1) suggest that the dominant adsorption mechanisms of glucosinolates on chitosan may be electrostatic attractions, including hydrogen bonds and charge neutralisation. Copyright © 2013 Elsevier Ltd. All rights reserved.
Ademiluyi, Adedayo O.; Oboh, Ganiyu; Agbebi, Oluwaseun J.; Akinyemi, Ayodele J.
This study sought to investigate the protective effect of dietary inclusion of Hibiscus sabdariffa calyx red dye on cisplatin-induced nephrotoxicity and antioxidant status in rats. Adult male rats were randomly divided into four groups of six animals each. Groups I and II were fed basal diet while groups III and IV were fed diets containing 0.5% and 1% of the dye respectively for 20 days prior to cisplatin administration. Nephrotoxicity was induced by a single dose intraperitoneal administration of cisplatin (7 mg/kg b.w) and the experiment was terminated 3 days after. The kidney and plasma were studied for nephrotoxicity and oxidative stress indices. Cisplatin administration caused a significant (P<0.05) increase in creatinine, uric acid, urea, and blood urea nitrogen (BUN) levels as well as kidney malondialdehyde (MDA) content, with concomitant decrease in kidney vitamin C and GSH contents. Furthermore, activities of kidney antioxidant enzymes such as, SOD, Catalase, and GST were significantly (P<0.05) altered in cisplatin administered rats. However, consumption of diets supplemented with the dye for 20 days prior to cisplatin administration protected the kidney and attenuates oxidative stress through modulation of in vivo antioxidant status. The determined anthocyanin content of the dye is 121.5 mg Cyanidin-3-rutinoside equivalent/100 g, thus, the observed nephroprotective effect of H. sabdariffa dye could be attributed to its anthocyanin content. PMID:24711761
Rodriguez Lanzi, Cecilia; de Rosas, Inés; Perdicaro, Diahann J; Ponce, María Teresa; Martinez, Liliana; Miatello, Roberto M; Cavagnaro, Bruno; Vazquez Prieto, Marcela A
We evaluated the effects of Syrah red wine treated with salicylic acid (RW SA) and its control red wine (RW) on metabolic parameters, systolic blood pressure and adipose tissue insulin signaling in high-fructose (F) fed rats. Grape treated with SA increased the anthocyanin (ANTs) levels in RW. F induced increased systolic blood pressure, dislipidemia and insulin resistance (HOMA:IR). F rats treated with RW significantly prevented these alterations while RW SA partially attenuated triglycerides levels and HOMA:IR without modifications in HDL cholesterol levels. F impaired the adipose tissue response to insulin. Supplementation with RW and RW SA partially attenuated these alterations. Rats supplemented with RW SA had lesser beneficial effects on metabolic alterations than control RW, while both RW and RW SA attenuated altered adipose response to insulin. More studies are necessary to deeply evaluate the effect on SA-induced RW rich in ANTs levels on metabolic alterations associated to MetS.
Takahashi, Azusa; Shimizu, Hisae; Okazaki, Yukako; Sakaguchi, Hirohide; Taira, Toshio; Suzuki, Takashi; Chiji, Hideyuki
Aronia fruits (chokeberry: Aronia melanocarpa E.) containing phenolic phytochemicals, such as cyanidin 3-glycosides and chlorogenic acid, have attracted considerable attention because of their potential human health benefits in humans including antioxidant activities and ability to improved vision. In the present study, the effects of anthocyanin-rich phytochemicals from aronia fruits (aronia phytochemicals) on visceral fat accumulation and fasting hyperglycemia were examined in rats fed a high-fat diet (Experiment 1). Total visceral fat mass was significantly lower in rats fed aronia phytochemicals than that in both the control group and bilberry phytochemicals-supplemented rats (p < 0.05). Moreover, perirenal and epididymal adipose tissue mass in rats fed aronia phytochemicals was significantly lower than that in both the control and bilberry phytochemicals group. Additionally, the mesenteric adipose tissue mass in aronia phytochemicals-fed rats was significantly low (p < 0.05). Furthermore, the fasting blood glucose levels significantly decreased in rats fed aronia phytochemicals for 4 weeks compared to that in the control rats (p < 0.05). Therefore, we investigated the effects of phytochemicals on postprandial hyperlipidemia after corn oil loading in rats, pancreatic lipase activity in vitro, and the plasma glycemic response after sucrose loading in order to elucidate the preventive factor of aronia phytochemical on visceral fat accumulation. In the oral corn oil tolerance tests (Experiment 2), aronia phytochemicals significantly inhibited the increases in plasma triglyceride levels, with a half-maximal inhibitory concentration (IC(50)) of 1.50 mg/mL. However, the inhibitory activity was similar to that of bilberry and tea catechins. In the sucrose tolerance tests (Experiment 3), aronia phytochemicals also significantly inhibited the increases in blood glucose levels that were observed in the control animals (p < 0.05). These results suggest that anthocyanin-rich
Poulose, Shibu M; Fisher, Derek R; Larson, Jessica; Bielinski, Donna F; Rimando, Agnes M; Carey, Amanda N; Schauss, Alexander G; Shukitt-Hale, Barbara
Age-related diseases of the brain compromise memory, learning, and movement and are directly linked with increases in oxidative stress and inflammation. Previous research has shown that supplementation with berries can modulate signaling in primary hippocampal neurons or BV-2 mouse microglial cells. Because of their high polyphenolic content, fruit pulp fractions of açai ( Euterpe oleracea Mart.) were explored for their protective effect on BV-2 mouse microglial cells. Freeze-dried açai pulp was fractionated using solvents with different polarities and analyzed using HPLC for major anthocyanins and other phenolics. Fractions extracted using methanol (MEOH) and ethanol (ETOH) were particularly rich in anthocyanins such as cyanidin, delphinidin, malvidin, pelargonidin, and peonidin, whereas the fraction extracted using acetone (ACE) was rich in other phenolics such as catechin, ferulic acid, quercetin, resveratrol, and synergic and vanillic acids. Studies were conducted to investigate the mitigating effects of açai pulp extracts on lipopolysaccharide (LPS, 100 ng/mL) induced oxidative stress and inflammation; treatment of BV-2 cells with acai fractions resulted in significant (p < 0.05) decreases in nitrite production, accompanied by a reduction in inducible nitric oxide synthase (iNOS) expression. The inhibition pattern was emulated with the ferulic acid content among the fractions. The protection of microglial cells by açai pulp extracts, particularly that of MEOH, ETOH, and ACE fractions, was also accompanied by a significant concentration-dependent reduction in cyclooxygenase-2 (COX-2), p38 mitogen-activated protein kinase (p38-MAPK), tumor necrosis factor-α (TNFα), and nuclear factor κB (NF-κB). The current study offers valuable insights into the protective effects of açai pulp fractions on brain cells, which could have implications for improved cognitive and motor functions.
Li, Li; Wu, Zhiqin; Yao, Lijun; Wu, Yonghou; Huang, Lian; Liu, Kan; Zhou, Xiang; Gou, Deming
Edible berries have a broad spectrum of biomedical functions, including improving immune responses and reducing risk for chronic diseases. In this study, the anti-inflammatory activities of crude extracts (CEs), anthocyanin-rich fractions (ARFs), and des-anthocyanin fractions (DAFs) from seven berries were evaluated based on their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)/IFN-γ-activated RAW264.7 macrophages. ARFs from red raspberries (RR-ARFs) exhibited the highest efficiency in suppressing NO synthesis. The anti-inflammatory properties were also demonstrated by reducing the expression levels of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), interleukin-1 beta (IL-1β) and IL-6 in RAW264.7 cells. The luciferase reporter assay demonstrated that the activities of NF-κB and AP-1 signaling pathways were significantly suppressed by RR-ARFs. Further studies showed that RR-ARFs decreased the phosphorylation of IKK, IκBα, p65 and JNK and the nuclear translocation of p65 in LPS/IFN-γ-stimulated RAW264.7 cells. In a mouse colitis model, dextran sulfate sodium (DSS)-induced weight loss and histological damage were significantly ameliorated by RR-ARFs treatment. Taken together, our results indicate that RR-ARFs attenuate inflammation both in vitro and in vivo primarily by inhibiting the activation of NF-κB and MAPKs. The anti-inflammatory of RR-ARFs could be harnessed and applied in animal agriculture, drug and food industries. PMID:25167935
Li, Li; Wang, Liyan; Wu, Zhiqin; Yao, Lijun; Wu, Yonghou; Huang, Lian; Liu, Kan; Zhou, Xiang; Gou, Deming
Edible berries have a broad spectrum of biomedical functions, including improving immune responses and reducing risk for chronic diseases. In this study, the anti-inflammatory activities of crude extracts (CEs), anthocyanin-rich fractions (ARFs), and des-anthocyanin fractions (DAFs) from seven berries were evaluated based on their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)/IFN-γ-activated RAW264.7 macrophages. ARFs from red raspberries (RR-ARFs) exhibited the highest efficiency in suppressing NO synthesis. The anti-inflammatory properties were also demonstrated by reducing the expression levels of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), interleukin-1 beta (IL-1β) and IL-6 in RAW264.7 cells. The luciferase reporter assay demonstrated that the activities of NF-κB and AP-1 signaling pathways were significantly suppressed by RR-ARFs. Further studies showed that RR-ARFs decreased the phosphorylation of IKK, IκBα, p65 and JNK and the nuclear translocation of p65 in LPS/IFN-γ-stimulated RAW264.7 cells. In a mouse colitis model, dextran sulfate sodium (DSS)-induced weight loss and histological damage were significantly ameliorated by RR-ARFs treatment. Taken together, our results indicate that RR-ARFs attenuate inflammation both in vitro and in vivo primarily by inhibiting the activation of NF-κB and MAPKs. The anti-inflammatory of RR-ARFs could be harnessed and applied in animal agriculture, drug and food industries.
Wang, Yong; Zhao, Liang; Wang, Dan; Huo, Yazhen; Ji, Baoping
Limited information is available regarding the relationship between the chemical structures and inhibitory effects of anthocyanin (ACN) on triglyceride (TG) overaccumulation. Thus this study investigated the antioxidant activity and inhibitory effect of blackberry, wild blueberry, strawberry, and chokeberry ACN-rich extracts, with different structural characteristics, on oleic acid-induced hepatic steatosis in vitro. Four major ACNs from these berries, with different aglycones, namely cyanidin-3-glucoside (Cy-3-glu), delphinidin-3-glucoside, pelargonidin-3-glucoside, and malvidin-3-glucoside, were also investigated. Blackberry ACN-rich extract exhibited the most significant inhibitory effect on TG clearance (30.5% ± 3.4%) and reactive oxygen species generation. TG clearance was significantly correlated with total phenolic content (r = 0.991, P < 0.05) and oxygen radical absorbance capacity value (r = 0.961, P < 0.05). Furthermore, Cy-3-glu showed the highest inhibitory effect on intracellular TG overaccumulation, with a maximum TG clearance of 61.3% at 40 µg mL(-1) . Our findings suggest that the inhibitory effects of different ACNs on oleic acid-induced hepatic steatosis significantly vary. Cy-3-glu, which contains the ortho hydroxyl group in its B ring, possibly confers the protective effects of antioxidants and inhibits TG accumulation in HepG2 cells. © 2015 Society of Chemical Industry. © 2015 Society of Chemical Industry.
Farhadi, Leila; Mohammadi-Motlagh, Hamid-Reza; Seyfi, Parivash; Mostafaie, Ali
Flavonoids are potentially immunomodulatory factors and it may be inferred that these phytochemicals contribute to immunomodulatory properties of the Allium family. In the present study, we investigated the potential mechanism underlying the immunomodulatory effect of shallot and its ethyl acetate (EA) fraction as flavonoid-rich sources. Ex vivo, effects of a hydroalcoholic extract of shallot, its fractions and quercetin on lymphocyte viability were evaluated. The proliferative effects of the fractions were examined using naive mouse lymphocytes to determine the fraction with highest impact/ activity. In addition, in a mouse model, both delayed- type hypersensitivity (DTH) responses and production of a key cytokine (interferon [IFN]-ᵧ) were evaluated. Both the shallot extract and its fractions inhibited lymphocytes cell growth and survival in a concentration- dependent manner. The findings also showed that the extract and especially the ethyl acetate (EA) fraction could induce lymphocyte proliferation. The evaluation of the extract and its EA fraction on DTH responses indicated that both caused a significant increase in DTH response. Furthermore, they triggered significant increases in IFNγ and decreases in interleukin (IL)-4 production by splenic mononuclear cells. Because of the significant immunomodulatory activity displayed in these studies, it is plausible that shallot could have a potential use as an immunomodulatory agent in clinical settings.
Farhadi, Leila; Mohammadi-Motlagh, Hamid-Reza; Seyfi, Parivash; Mostafaie, Ali
Flavonoids are potentially immunomodulatory factors and it may be inferred that these phytochemicals contribute to immunomodulatory properties of the Allium family. In the present study, we investigated the potential mechanism underlying the immunomodulatory effect of shallot and its ethyl acetate (EA) fraction as flavonoid-rich sources. Ex vivo, effects of a hydroalcoholic extract of shallot, its fractions and quercetin on lymphocyte viability were evaluated. The proliferative effects of the fractions were examined using naive mouse lymphocytes to determine the fraction with highest impact/ activity. In addition, in a mouse model, both delayed- type hypersensitivity (DTH) responses and production of a key cytokine (interferon [IFN]-ᵧ) were evaluated. Both the shallot extract and its fractions inhibited lymphocytes cell growth and survival in a concentration- dependent manner. The findings also showed that the extract and especially the ethyl acetate (EA) fraction could induce lymphocyte proliferation. The evaluation of the extract and its EA fraction on DTH responses indicated that both caused a significant increase in DTH response. Furthermore, they triggered significant increases in IFNγ and decreases in interleukin (IL)-4 production by splenic mononuclear cells. Because of the significant immunomodulatory activity displayed in these studies, it is plausible that shallot could have a potential use as an immunomodulatory agent in clinical settings. PMID:24551817
Pereira, Sónia R; Pereira, Rita; Figueiredo, Isabel; Freitas, Victor; Dinis, Teresa C P; Almeida, Leonor M
Despite the actual therapeutic approaches for inflammatory bowel disease (IBD), efficient and secure alternative options remain a research focus. In this context, anthocyanins seem promising natural anti-inflammatory agents, but their action mechanisms and efficacy as compared with established drugs still require more clarification. The main aim of this study was to compare the anti-inflammatory action of a chemically characterized anthocyanin-rich fraction (ARF), obtained from Portuguese blueberries (Vaccinium corymbosum L.), with that of 5-aminosalicylic acid (5-ASA), a first-line drug in IBD, in a 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis rat model. Such fraction showed a high content and great molecular diversity of anthocyanins, with malvidin-3-galactoside and petunidin-3-arabinoside in the highest concentrations. After daily administration by intragastric infusion for 8 days, ARF, at a molar anthocyanin concentration about 30 times lower than 5-ASA, showed a higher effectiveness in counteracting the intestinal inflammation, as assessed by i) body weight variation and colon damage score, ii) reduction in leukocyte infiltration, iii) increase in antioxidant defenses and iv) by downregulation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in colon tissue homogenates. The strong inhibition of COX-2 expression seems to be a crucial anti-inflammatory mechanism common to both ARF and 5-ASA, but the additional higher abilities of anthocyanins to downregulate iNOS and to decrease leukocytes infiltration and to increase antioxidant defenses in colon may account for the much higher anti-inflammatory action of anthocyanins. These data may contribute to the development of a promising natural approach in IBD management.
Pereira, Sónia R.; Pereira, Rita; Figueiredo, Isabel; Freitas, Victor; Dinis, Teresa C. P.; Almeida, Leonor M.
Despite the actual therapeutic approaches for inflammatory bowel disease (IBD), efficient and secure alternative options remain a research focus. In this context, anthocyanins seem promising natural anti-inflammatory agents, but their action mechanisms and efficacy as compared with established drugs still require more clarification. The main aim of this study was to compare the anti-inflammatory action of a chemically characterized anthocyanin-rich fraction (ARF), obtained from Portuguese blueberries (Vaccinium corymbosum L.), with that of 5-aminosalicylic acid (5-ASA), a first-line drug in IBD, in a 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis rat model. Such fraction showed a high content and great molecular diversity of anthocyanins, with malvidin-3-galactoside and petunidin-3-arabinoside in the highest concentrations. After daily administration by intragastric infusion for 8 days, ARF, at a molar anthocyanin concentration about 30 times lower than 5-ASA, showed a higher effectiveness in counteracting the intestinal inflammation, as assessed by i) body weight variation and colon damage score, ii) reduction in leukocyte infiltration, iii) increase in antioxidant defenses and iv) by downregulation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in colon tissue homogenates. The strong inhibition of COX-2 expression seems to be a crucial anti-inflammatory mechanism common to both ARF and 5-ASA, but the additional higher abilities of anthocyanins to downregulate iNOS and to decrease leukocytes infiltration and to increase antioxidant defenses in colon may account for the much higher anti-inflammatory action of anthocyanins. These data may contribute to the development of a promising natural approach in IBD management. PMID:28329021
Alvarez-Suarez, José M; Giampieri, Francesca; Tulipani, Sara; Casoli, Tiziana; Di Stefano, Giuseppina; González-Paramás, Ana M; Santos-Buelga, Celestino; Busco, Franco; Quiles, Josè L; Cordero, Mario D; Bompadre, Stefano; Mezzetti, Bruno; Battino, Maurizio
Strawberries are an important fruit in the Mediterranean diet because of their high content of essential nutrients and beneficial phytochemicals, which seem to exert beneficial effects in human health. Healthy volunteers were supplemented daily with 500 g of strawberries for 1 month. Plasma lipid profile, circulating and cellular markers of antioxidant status, oxidative stress and platelet function were evaluated at baseline, after 30 days of strawberry consumption and 15 days after the end of the study. A high concentration of vitamin C and anthocyanins was found in the fruits. Strawberry consumption beneficially influenced the lipid profile by significantly reducing total cholesterol, low-density lipoprotein cholesterol and triglycerides levels (-8.78%, -13.72% and -20.80%, respectively; P<.05) compared with baseline period, while high-density lipoprotein cholesterol remained unchanged. Strawberry supplementation also significant decreased serum malondialdehyde, urinary 8-OHdG and isoprostanes levels (-31.40%, -29.67%, -27.90%, respectively; P<.05). All the parameters returned to baseline values after the washout period. A significant increase in plasma total antioxidant capacity measured by both ferric reducing ability of plasma and oxygen radical absorbance capacity assays and vitamin C levels (+24.97%, +41.18%, +41.36%, respectively; P<.05) was observed after strawberry consumption. Moreover, the spontaneous and oxidative hemolysis were significant reduced (-31.7% and -39.03%, respectively; P<.05), compared to the baseline point, which remained stable after the washout period. Finally, strawberry intake significant decrease (P<.05) the number of activated platelets, compared to both baseline and washout values. Strawberries consumption improves plasma lipids profile, biomarkers of antioxidant status, antihemolytic defenses and platelet function in healthy subjects, encouraging further evaluation on a population with higher cardiovascular disease risk.
Poulose, Shibu M.; Rabin, Bernard M.; Bielinski, Donna F.; Kelly, Megan E.; Miller, Marshall G.; Thanthaeng, Nopporn; Shukitt-Hale, Barbara
The protective effects of anthocyanin-rich blueberries (BB) on brain health are well documented and are particularly important under conditions of high oxidative stress, which can lead to ;accelerated aging.; One such scenario is exposure to space radiation, consisting of high-energy and -charge particles (HZE), which are known to cause cognitive dysfunction and deleterious neurochemical alterations. We recently tested the behavioral and neurochemical effects of acute exposure to HZE particles such as 56Fe, within 24-48 h after exposure, and found that radiation primarily affects memory and not learning. Importantly, we observed that specific brain regions failed to upregulate antioxidant and anti-inflammatory mechanisms in response to this insult. To further examine these endogenous response mechanisms, we have supplemented young rats with diets rich in BB, which are known to contain high amounts of antioxidant-phytochemicals, prior to irradiation. Exposure to 56Fe caused significant neurochemical changes in hippocampus and frontal cortex, the two critical regions of the brain involved in cognitive function. BB supplementation significantly attenuated protein carbonylation, which was significantly increased by exposure to 56Fe in the hippocampus and frontal cortex. Moreover, BB supplementation significantly reduced radiation-induced elevations in NADPH-oxidoreductase-2 (NOX2) and cyclooxygenase-2 (COX-2), and upregulated nuclear factor erythroid 2-related factor 2 (Nrf2) in the hippocampus and frontal cortex. Overall results indicate that 56Fe particles may induce their toxic effects on hippocampus and frontal cortex by reactive oxygen species (ROS) overload, which can cause alterations in the neuronal environment, eventually leading to hippocampal neuronal death and subsequent impairment of cognitive function. Blueberry supplementation provides an effective preventative measure to reduce the ROS load on the CNS in an event of acute HZE exposure.
Poulose, Shibu M; Rabin, Bernard M; Bielinski, Donna F; Kelly, Megan E; Miller, Marshall G; Thanthaeng, Nopporn; Shukitt-Hale, Barbara
The protective effects of anthocyanin-rich blueberries (BB) on brain health are well documented and are particularly important under conditions of high oxidative stress, which can lead to "accelerated aging." One such scenario is exposure to space radiation, consisting of high-energy and -charge particles (HZE), which are known to cause cognitive dysfunction and deleterious neurochemical alterations. We recently tested the behavioral and neurochemical effects of acute exposure to HZE particles such as (56)Fe, within 24-48h after exposure, and found that radiation primarily affects memory and not learning. Importantly, we observed that specific brain regions failed to upregulate antioxidant and anti-inflammatory mechanisms in response to this insult. To further examine these endogenous response mechanisms, we have supplemented young rats with diets rich in BB, which are known to contain high amounts of antioxidant-phytochemicals, prior to irradiation. Exposure to (56)Fe caused significant neurochemical changes in hippocampus and frontal cortex, the two critical regions of the brain involved in cognitive function. BB supplementation significantly attenuated protein carbonylation, which was significantly increased by exposure to (56)Fe in the hippocampus and frontal cortex. Moreover, BB supplementation significantly reduced radiation-induced elevations in NADPH-oxidoreductase-2 (NOX2) and cyclooxygenase-2 (COX-2), and upregulated nuclear factor erythroid 2-related factor 2 (Nrf2) in the hippocampus and frontal cortex. Overall results indicate that (56)Fe particles may induce their toxic effects on hippocampus and frontal cortex by reactive oxygen species (ROS) overload, which can cause alterations in the neuronal environment, eventually leading to hippocampal neuronal death and subsequent impairment of cognitive function. Blueberry supplementation provides an effective preventative measure to reduce the ROS load on the CNS in an event of acute HZE exposure.
Anthocyanins are the red, blue, and purple pigments present throughout nature. Foods rich in anthocyanins include berries, red cabbage, radish, eggplant, blue corn, and purple carrots, as well as many other red, purple, and blue fruits, vegetables, and legumes. Evidence continues to accumulate sugg...
Because of its intense anthocyanin pigments, black raspberry (Rubus occidentalis L.) has a long history of use as a natural colorant and dye. Recent studies showing black raspberries to be a rich source of anthocyanins and other dietary phytochemicals have led to renewed interest in breeding better ...
Kamonpatana, Kom; Giusti, M. Mónica; Chitchumroonchokchai, Chureeporn; MorenoCruz, Maria; Riedl, Ken M.; Kumar, Purnima; Failla, Mark L.
Some fruits and their anthocyanin-rich extracts have been reported to exhibit chemopreventive activity in the oral cavity. Insights regarding oral metabolism of anthocyanins remain limited. Anthocyanin-rich extracts from blueberry, chokeberry, black raspberry, red grape, and strawberry were incubated ex vivo with human saliva from 14 healthy subjects. All anthocyanins were partially degraded in saliva. Degradation of chokeberry anthocyanins in saliva was temperature dependent and decreased by heating saliva to 80 °C and after removal of cells. Glycosides of delphinidin and petunidin were more susceptible to degradation than those of cyanidin, pelargonidin, peonidin and malvidin in both intact and artificial saliva. Stability of di- and tri-saccharide conjugates of anthocyanidins slightly, but significantly, exceeded that of monosaccharide compounds. Ex vivo degradation of anthocyanins in saliva was significantly decreased after oral rinsing with antibacterial chlorhexidine. These results suggest that anthocyanin degradation in the mouth is structure-dependent and largely mediated by oral microbiota. PMID:22868153
Fredericks, Charissa H; Fanning, Kent J; Gidley, Michael J; Netzel, Gabriele; Zabaras, Dimitrios; Herrington, Mark; Netzel, Michael
Diets high in fruit and vegetables are known to have significant health benefits. This is in part due to the presence of phytochemicals, which possess potential protective health benefits. This study focuses on the ability of strawberries to be bred for higher anthocyanin content. This is a major contributor to the characteristic colour and nutritional value of ripe strawberries, together with phenolic acids, ascorbic acid and total antioxidant capacity. Anthocyanins in five commercial strawberry cultivars and three breeding lines were assessed. This led to the discovery of one breeding line (BL 2006-221) as an exceptional source of anthocyanins (~1 g kg(-1) fresh weight), with approximately double the levels of current commercial cultivars. Temperature was shown to influence anthocyanin extraction, with 40 °C being the best extraction temperature using the accelerated solvent extraction (ASE) method. Hue angle and anthocyanin concentration showed a good correlation (r(2) = 0.69). The new breeding line BL 2006-221 has the potential to be used in the development of phytochemically rich strawberry cultivars. Using hue angle as a screening tool for total anthocyanin concentration and extraction of anthocyanins from strawberries by ASE at 40 °C would support such cultivar development. © 2012 Commonwealth of Australia.
da Silva Santos, Vivian; Bisen-Hersh, Emily; Yu, Yingchun; Cabral, Ingridy Simone Ribeiro; Nardini, Viviani; Culbreth, Megan; Teixeira da Rocha, João Batista; Barbosa, Fernando; Aschner, Michael
Manganese (Mn) is an essential element for human health. However, at high concentrations Mn may be neurotoxic. Mn accumulates in astrocytes, affecting their redox status. In view of the high antioxidant and anti-inflammatory properties of the exotic Brazilian fruit açaí (Euterpe oleracea Mart.), its methanolic extract was obtained by solid-phase extraction (SPE). This açaí extract showed considerable anthocyanins content and direct antioxidant capacity. The açaí extract scavenged 2,2-diphenyl-1-picrylhydrazyl radicals (DPPH•) with an EC₅₀ of 19.1 ppm, showing higher antioxidant activity compared to butylated hydroxytoluene (BHT), but lower than ascorbic acid and quercetin. This obtained açaí extract also attenuated Mn-induced oxidative stress in primary cultured astrocytes. Specifically, the açaí extract at an optimal and nutritionally relevant concentration of 0.1 μg/ml prevented Mn-induced oxidative stress by (1) restoring GSH/GSSG ratio and net glutamate uptake, (2) protecting astrocytic membranes from lipid peroxidation, and (3) decreasing Mn-induced expression of erythroid 2-related factor (Nrf2) protein. A larger quantity of açaí extract exacerbated the effects of Mn on these parameters except with respect to lipid peroxidation assessed by means of F₂-isoprostanes. These studies indicate that at nutritionally relevant concentration, anthocyanins obtained from açaí protect astrocytes against Mn neurotoxicity, but at high concentrations, the "pro-oxidant" effects of its constituents likely prevail. Future studies may be profitably directed at potential protective effects of açaí anthocyanins in nutraceutical formulations.
The kinetics of anthocyanin metabolism was investigated in a human feeding trial. Volunteers (n=12) consumed purple carrots containing five different anthocyanin forms: cyanidin-3-(2”-xylose-6”-glucose-galactoside), cyanidin-3-(2”-xylose-galactoside), cyanidin-3-(2”-xylose-6”-sinapoyl-glucose-galac...
Anthocyanins, a sub-class of flavonoids, are natural pigments known to have functional health benefits. Sorghum is a rich source of various phytochemicals including anthocyanins. This study was to identify and quantify the profiles of anthocyanins by HPLC-DAD in the selected 25 sorghum accessions wi...
McGhie, Tony K; Walton, Michaela C
Evidence that anthocyanin compounds have beneficial effects for health are increasingly being reported in the scientific literature and these compounds are now widely recognised as potential therapeutic compounds. Berry fruit are rich sources of anthocyanins and berry fruit products or derived beverages can provide 10s to 100s of milligrams of anthocyanins in a single serve. Anthocyanins exhibit complex chemical behaviours in vitro and this will result in complex behaviour in vivo. This review attempts to summarize some aspects of anthocyanin biochemistry and discusses these in the context of what is currently known about bioavailability and absorption. Compared with other flavonoid groups, such as flavonols, relatively little is known about details and mechanisms of anthocyanin absorption and transport and much remains to be discovered.
Zhang, Yanjie; Chen, Guoping; Dong, Tingting; Pan, Yu; Zhao, Zhiping; Tian, Shibing; Hu, Zongli
Bok choy (Brassica rapa var. chinensis) is an important dietary vegetable cultivated and consumed worldwide for its edible leaves. The purple cultivars rich in health-promoting anthocyanins are usually more eye-catching and valuable. Fifteen kinds of anthocyanins were separated and identified from a purple bok choy cultivar (Zi He) by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. To investigate the molecular mechanisms underlying anthocyanin accumulation in bok choy, the expression profiles of anthocyanin biosynthetic and regulatory genes were analyzed in seedlings and leaves of the purple cultivar and the green cultivar (Su Zhouqing). Compared with the other tissues, BrTT8 and most of the anthocyanin biosynthetic genes were significantly up-regulated in the leaves and light-grown seedlings of Zi He. The results that heterologous expression of BrTT8 promotes the transcription of partial anthocyanin biosynthetic genes in regeneration shoots of tomato indicate that BrTT8 plays an important role in the regulation of anthocyanin biosynthesis.
Lou, Qian; Wang, Lin; Liu, Hongli; Liu, Yali
Grape hyacinth (Muscari spp.) is a popular ornamental bulbous perennial famous for its blue flowers. To understand the chemical basis of the rich blue colors in this plant, anthocyanin profiles of six blue flowering grape hyacinths as well as one pink and one white cultivar were determined using high-performance liquid chromatography and mass spectrometry. Along with two known compounds, eight putative anthocyanins were identified in the tepals of grape hyacinth for the first time. The accumulation and distribution of anthocyanins in the plant showed significant cultivar and flower development specificity. Violet-blue flowers mainly contained simple delphinidin-type anthocyanins bearing one or two methyl-groups but no acyl groups, whereas white and pink flowers synthesised more complex pelargonidin/cyanidin-derivatives with acyl-moieties but no methyl-groups. The results partially reveal why solid blue, orange or red flowers are rare in this plant in nature. In addition, pelargonidin-type anthocyanins were found for the first time in the genus, bringing more opportunities in terms of breeding of flower color in grape hyacinth.
Afaq, Farrukh; Saleem, Mohammad; Krueger, Christian G; Reed, Jess D; Mukhtar, Hasan
Chemoprevention has come of age as an effective cancer control modality; however, the search for novel agent(s) for the armamentarium of cancer chemoprevention continues. We argue that agents capable of intervening at more than one critical pathway in the carcinogenesis process will have greater advantage over other single-target agents. Pomegranate fruit extract (PFE) derived from the tree Punica granatum possesses strong antioxidant and antiinflammatory properties. Pomegranate fruit was extracted with acetone and analyzed based on matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and found to contain anthocyanins, ellagitannins and hydrolyzable tannins. We evaluated whether PFE possesses antitumor-promoting effects. We first determined the effect of topical application of PFE to CD-1 mice against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced conventional markers and other novel markers of skin tumor promotion. We found that topical application of PFE (2 mg/mouse) 30 min prior to TPA (3.2 nmole/mouse) application on mouse skin afforded significant inhibition, in a time-dependent manner, against TPA-mediated increase in skin edema and hyperplasia, epidermal ornithine decarboxylase (ODC) activity and protein expression of ODC and cyclooxygenase-2. We also found that topical application of PFE resulted in inhibition of TPA-induced phosphorylation of ERK1/2, p38 and JNK1/2, as well as activation of NF-kappaB and IKKalpha and phosphorylation and degradation of IkappaBalpha. We next assessed the effect of skin application of PFE on TPA-induced skin tumor promotion in 7,12-dimethylbenz(a)anthracene-initiated CD-1 mouse. The animals pretreated with PFE showed substantially reduced tumor incidence and lower tumor body burden when assessed as total number of tumors per group, percent of mice with tumors and number of tumors per animal as compared to animals that did not receive PFE. In TPA-treated group, 100% of the mice developed tumors at
Esselen, Melanie; Boettler, Ute; Teller, Nicole; Bachler, Simone; Hutter, Melanie; Rufer, Corinna E; Skrbek, Susanne; Marko, Doris
In the present study, we addressed the question whether cyanidin-3-glucoside (C3G) or complex C3G-rich blackberry extracts affect human topoisomerases with special emphasis on the contribution of the potential degradation products phloroglucinol aldehyde (PGA) and protocatechuic acid (PCA). In HT29 colon carcinoma cells a C3G-rich blackberry extract suppressed camptothecin- (CPT-) or doxorubicin- (DOX-) induced stabilization of the covalent DNA-topoisomerase intermediate, thus antagonizing the effects of these classical topoisomerase poisons on DNA integrity. As a single compound, C3G (100 μM) decreased the DNA-damaging effects of CPT as well, but did not significantly affect those induced by DOX. At the highest applied concentration (100 μM), cyanidin protected DNA from CPT- and DOX-induced damage. Earlier reports on DNA-damaging properties of cyanidin were found to result most likely from the formation of hydrogen peroxide as an artifact in the cell culture medium when the incubation was performed in the absence of catalase. The suppression of hydrogen peroxide accumulation, achieved by the addition of catalase, demonstrated that cyanidin does not exhibit DNA-damaging properties in HT29 cells (up to 100 μM). The observed effects on topoisomerase interference and DNA protection against CPT or DOX were clearly limited to the parent compound and were not observed for the potential cyanidin degradation products PGA and PCA.
He, Qiong; Zhang, Zhanfeng; Zhang, Lugang
Heading Chinese cabbage (Brassica rapa L. ssp. pekinensis) is a significant dietary vegetable for its edible heading leaves in Asia countries. The new purple anthocyanin-rich pure line (11S91) was successfully bred, and the anthocyanins were mainly distributed in 2-3 cell layers beneath the leaf epidermis, whereas siliques and stems accumulated only a cell layer of anthocyanins. The anthocyanins of 11S91 were more stable at pHs below 3.0 and temperatures below 45 °C. The total antioxidant ability was highly positive correlated with the anthocyanin content in 11S91. Thirty-two anthocyanins were separated and identified, and 70% of them were glycosylated and acylated cyanidins. The four major anthocyanins present were cyanidin-3-sophoroside(p-coumaroyl)-5-glucoside(malonyl), cyanidin-3-sophoroside(ferulyl)-5-glucoside(malonyl), cyanidin-3-sophoroside(sinapyl-p-coumaroyl)-5-glucoside(malonyl), and cyanidin-3-sophoroside-(sinapyl-ferulyl)-5-glucoside(malonyl). According to the expression of biosynthetic genes and the component profile of anthocyanins in 11S91 and its parents, regulatory genes BrMYB2 and BrTT8 probably activate the anthocyanin biosynthesis but other factors may govern the primary anthocyanins and the distribution.
Muleke, Everlyne M'mbone; Fan, Lianxue; Wang, Yan; Xu, Liang; Zhu, Xianwen; Zhang, Wei; Cao, Yang; Karanja, Benard K.; Liu, Liwang
Anthocyanins are natural pigments that have important functions in plant growth and development. Radish taproots are rich in anthocyanins which confer different taproot colors and are potentially beneficial to human health. The crop differentially accumulates anthocyanin during various stages of growth, yet molecular mechanisms underlying this differential anthocyanin accumulation remains unknown. In the present study, transcriptome analysis was used to concisely identify putative genes involved in anthocyanin biosynthesis in radish. Spatial-temporal transcript expressions were then profiled in four color variant radish cultivars. From the total transcript sequences obtained through illumina sequencing, 102 assembled unigenes, and 20 candidate genes were identified to be involved in anthocyanin biosynthesis. Fifteen genomic sequences were isolated and sequenced from radish taproot. The length of these sequences was between 900 and 1,579 bp, and the unigene coverage to all of the corresponding cloned sequences was more than 93%. Gene structure analysis revealed that RsF3′H is intronless and anthocyanin biosynthesis genes (ABGs) bear asymmetrical exons, except RsSAM. Anthocyanin accumulation showed a gradual increase in the leaf of the red radish and the taproot of colored cultivars during development, with a rapid increase at 30 days after sowing (DAS), and the highest content at maturity. Spatial-temporal transcriptional analysis of 14 genes revealed detectable expressions of 12 ABGs in various tissues at different growth levels. The investigation of anthocyanin accumulation and gene expression in four color variant radish cultivars, at different stages of development, indicated that total anthocyanin correlated with transcript levels of ABGs, particularly RsUFGT, RsF3H, RsANS, RsCHS3 and RsF3′H1. Our results suggest that these candidate genes play key roles in phenotypic and spatial-temporal anthocyanin accumulation in radish through coordinated regulation and
Muleke, Everlyne M'mbone; Fan, Lianxue; Wang, Yan; Xu, Liang; Zhu, Xianwen; Zhang, Wei; Cao, Yang; Karanja, Benard K; Liu, Liwang
Anthocyanins are natural pigments that have important functions in plant growth and development. Radish taproots are rich in anthocyanins which confer different taproot colors and are potentially beneficial to human health. The crop differentially accumulates anthocyanin during various stages of growth, yet molecular mechanisms underlying this differential anthocyanin accumulation remains unknown. In the present study, transcriptome analysis was used to concisely identify putative genes involved in anthocyanin biosynthesis in radish. Spatial-temporal transcript expressions were then profiled in four color variant radish cultivars. From the total transcript sequences obtained through illumina sequencing, 102 assembled unigenes, and 20 candidate genes were identified to be involved in anthocyanin biosynthesis. Fifteen genomic sequences were isolated and sequenced from radish taproot. The length of these sequences was between 900 and 1,579 bp, and the unigene coverage to all of the corresponding cloned sequences was more than 93%. Gene structure analysis revealed that RsF3'H is intronless and anthocyanin biosynthesis genes (ABGs) bear asymmetrical exons, except RsSAM. Anthocyanin accumulation showed a gradual increase in the leaf of the red radish and the taproot of colored cultivars during development, with a rapid increase at 30 days after sowing (DAS), and the highest content at maturity. Spatial-temporal transcriptional analysis of 14 genes revealed detectable expressions of 12 ABGs in various tissues at different growth levels. The investigation of anthocyanin accumulation and gene expression in four color variant radish cultivars, at different stages of development, indicated that total anthocyanin correlated with transcript levels of ABGs, particularly RsUFGT, RsF3H, RsANS, RsCHS3 and RsF3'H1. Our results suggest that these candidate genes play key roles in phenotypic and spatial-temporal anthocyanin accumulation in radish through coordinated regulation and the
Ku, Ping-Kaung; Mancinelli, Alberto L.
Red far red reversibility (phytochrome control) of anthocyanin synthesis can be easily demonstrated for the response induced by short (5 minutes) and relatively short (4 hours) irradiation. Red far red reversibility of the response induced by longer irradiations can be demonstrated by the use of cyclic irradiations alternating short exposures to red and far red light. The level of anthocyanin formed during the dark incubation period following exposure to light depends upon the duration of the irradiation and becomes proportionally smaller as the length of the irradiation increases. Production of anthocyanins under cyclic irradiations depends upon the total energy applied and upon the length of the dark interval between successive irradiations. The relative efficiencies of radiations in various spectral ranges change with changes in the length of the irradiations. PMID:16657927
Because of its intense anthocyanin pigments, black raspberry (Rubus occidentalis L.) has a long history of use as a natural colorant and dye. Recent studies showing black raspberries to be a rich source of anthocyanins and other dietary phytochemicals has led to renewed interest in breeding new, bet...
Plant derived anthocyanin rich foods play a protective role against chronic diseases such as diabetes, obesity, cardiovascular, cancer and neurodegenerative diseases. Anthocyanins are absorbed in their intact form and can be metabolized to a wide array of phenolic metabolites/conjugates. Blueberries...
Santos-Buelga, Celestino; Mateus, Nuno; De Freitas, Victor
Anthocyanins are plant pigments widespread in nature. They play relevant roles in plant propagation and ecophysiology and plant defense mechanisms and are responsible for the color of fruits and vegetables. A large number of novel anthocyanin structures have been identified, including new families such as pyranoanthocyanins or anthocyanin oligomers; their biosynthesis pathways have been elucidated, and new plants with "a la carte" colors have been created by genetic engineering. Furthermore, evidence about their benefits in human health has accumulated, and processes of anthocyanin absorption and biotransformation in the human organism have started to be ascertained. These advances in anthocyanin research were revised in the Seventh International Workshop on Anthocyanins that took place in Porto (Portugal) on September 9-11, 2013. Some selected papers are collected in this special issue, where aspects such as anthocyanin accumulation in plants, relationship with color expression, stability in plants and food, and bioavailability or biological activity are revised.
Bimpilas, Andreas; Panagopoulou, Marilena; Tsimogiannis, Dimitrios; Oreopoulou, Vassiliki
Copigmentation of anthocyanins accounts for over 30% of fresh red wine color, while during storage, the color of polymeric pigments formed between anthocyanins and proanthocyanidins predominates. Rosmarinic acid and natural extracts rich in hydroxycinnamic acids, obtained from aromatic plants (Origanum vulgare and Satureja thymbra), were examined as cofactors to fresh Merlot wine and the effect on anthocyanin copigmentation and wine color was studied during storage for 6months. An increase of the copigmented anthocyanins that enhanced color intensity by 15-50% was observed, confirming the ability of complex hydroxycinnamates to form copigments. The samples with added cofactors retained higher percentages of copigmented anthocyanins and higher color intensity, compared to the control wine, up to 3 months. However, the change in the equilibrium between monomeric and copigmented anthocyanins that was induced by added cofactors, did not affect the rate of polymerization reactions during storage. Copyright © 2015 Elsevier Ltd. All rights reserved.
Ferrer-Gallego, Raúl; Soares, Susana; Mateus, Nuno; Rivas-Gonzalo, Julián; Escribano-Bailón, M Teresa; de Freitas, Victor
The interaction between phenolic compounds and salivary proteins is considered the basis of the poorly understood phenomenon of astringency. Furthermore, this interaction is an important factor in relation to their bioavailability. In this work, interactions between anthocyanin and human salivary protein fraction were studied by mass spectrometry (MALDI-TOF-MS and FIA-ESI-MS) and saturation-transfer difference (STD) NMR spectroscopy. Anthocyanins were able to interact with saliva proteins. The dissociation constant (KD) between malvidin 3-glucoside and salivary proline-rich proteins was 1.92 mM for the hemiketal form (pH 3.4) and 1.83 mM for the flavylium cation (pH 1.0). New soluble complexes between these salivary proteins and malvidin 3-glucoside were identified for the first time.
Vaccinium fruit ingredients within dietary supplements were identified by comparisons with anthocyanin analyses of known Vaccinium profiles (demonstration of anthocyanin fingerprinting). Available Vaccinium supplements were purchased and analyzed; their anthocyanin profiles (based on HPLC separation...
Nankar, Amol N; Dungan, Barry; Paz, Neil; Sudasinghe, Nilusha; Schaub, Tanner; Holguin, F Omar; Pratt, Richard C
Anthocyanin-rich blue corn is an emerging specialty crop in the USA. The antioxidant properties of blue corn offer health benefits in the human diet. The objectives of this study were to identify, characterize and quantify the anthocyanins from blue corn. Hypotheses tested were that total anthocyanin content was similar among southwestern US accessions and that it would vary across locations. It was also examined whether different anthocyanin components were unique to certain genotypes. Across all locations and accessions, an average of 0.43 g kg(-1) total anthocyanin content (TAC) was observed. Accessions Santa Clara Blue and Ohio Blue displayed the highest TAC. The TAC of accession Flor del Rio was lower by nearly a factor of six. A total of five anthocyanin components were identified. Cyanidin 3-glucoside was the most abundant, followed by pelargonidin and peonidin 3-glucoside. Succinyl and disuccinyl glycosidic forms of cyanidin were also identified. Cyanidin 3-disuccinylglucoside was newly identified as a novel form of anthocyanin. Quantitative and qualitative anthocyanin expression was determined to be relatively stable across multiple southwestern environments. Increased expression of red and purple pigmentation in accession Flor del Rio appeared to be associated more with reduced TAC and cyanidin 3-glucoside than with elevated pelargonidin per se. A previously unreported anthocyanin component in blue corn, cyanidin 3-disuccinylglucoside, is present in southwestern landraces. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.
Qi, Xiwu; Shuai, Qin; Chen, Hu; Fan, Li; Zeng, Qiwei; He, Ningjia
Anthocyanins are natural food colorants produced by plants that play important roles in their growth and development. Mulberry fruits are rich in anthocyanins, which are the most important active components of mulberry and have many potentially beneficial effects on human health. The study of anthocyanin biosynthesis will bring benefits for quality improvement and industrial exploration of mulberry fruits. In the present study, nine putative genes involved in anthocyanin biosynthesis in mulberry plants were identified and cloned. Sequence analysis revealed that the mulberry anthocyanin biosynthetic genes were conserved and had counterparts in other plants. Spatial transcriptional analysis showed detectable expression of eight of these genes in different tissues. The results of expression and UPLC analyses in two mulberry cultivars with differently colored fruit indicated that anthocyanin concentrations correlated with the expression levels of genes associated with anthocyanin biosynthesis including CHS1, CHI, F3H1, F3'H1, and ANS during the fruit ripening process. The present studies provide insight into anthocyanin biosynthesis in mulberry plants and may facilitate genetic engineering for improvement of the anthocyanin content in mulberry fruit.
Motohashi, Noboru; Sakagami, Hiroshi
Anthocyanins, a proanthocyanidin-type of flavonoid, contain an abundance of functional phytochemicals and occur in fruits such as cranberry, blueberry, orange, apple and in vegetables such as tomato, sweet pepper, spinach, and radishes. Functional and essential diets have been ingested in daily life since the primitive era of history. When anthocyanins are coupled with some water-soluble sugar molecules, their color becomes red, yellow, violet, or blue. It is very intriguing that anthocyanins provide the colorful variety of pigments for pansies, petunias, plums, and other diverse flowers. Chlorophyll in various fruits and vegetables is the main green phyto-component, while anthocyanins are probably the most important visible plant pigments in the natural kingdom having specific colors. Anthocyanins have been clinically used in many folklore medicines worldwide. Anthocyanins could provide health benefits for age-related diseases as well as other diseases. Anthocyanins have higher antioxidant capacity against oxidative stress induced by excess reactive oxygen species (ROS) such as superoxide radicals, hydrogen peroxide, and thus the human body might be protected from oxidative injury by anthocyanins. On the basis of these facts, we review the synthesis of plant flavonoids and their ability to scavenge oxidants, inhibit or activate enzymes, and the safety of proanthocyanidins and anthocyanidins present in common foods.
Wallace, Taylor C.; Slavin, Margaret; Frankenfeld, Cara L.
Anthocyanins are dietary flavonoids commonly consumed in the diet, which have been suggested to have a preventative effect on cardiovascular disease (CVD) development among epidemiological studies. We systematically reviewed randomized controlled trials (RCTs) testing the effects of purified anthocyanins and anthocyanin-rich extracts on markers of CVD (triglycerides, total cholesterol, low-density lipoprotein (LDL) cholesterol, high-density lipoprotein (HDL) cholesterol, and blood pressure) in both healthy and diseased populations. Eligible studies included RCTs of adults published in English. We searched PubMed, Web of Science Core Collection, and BIOSIS Previews for relevant articles from inception until 1 July 2014. Twelve RCTs representing 10 studies were included in this review. Supplementation with anthocyanins significantly improved LDL cholesterol among diseased individuals or those with elevated biomarkers. Supplementation did not significantly affect other markers of CVD in either healthy individuals or those with elevated markers. No adverse effects of anthocyanins were reported across studies at levels up to 640 mg/day. Limitations of trials in the qualitative analyses include short trial duration and large variability in the dose administered within the trials. Longer-duration trials assessing dose response are needed to adequately determine whether an effect of supplementation exists. PMID:26761031
Zoratti, Laura; Sarala, Marian; Carvalho, Elisabete; Karppinen, Katja; Martens, Stefan; Giongo, Lara; Häggman, Hely; Jaakola, Laura
Light is one of the most significant environmental factors affecting to the accumulation of flavonoids in fruits. The composition of the light spectrum has been shown to affect the production of phenolic compounds during fruit ripening. However, specific information on the biosynthesis of flavonoids in fruits in response to different wavelengths of light is still scarce. In the present study bilberry (Vaccinium myrtillus L.) fruits, which are known to be rich with anthocyanin compounds, were illuminated with blue, red, far-red or white light during the berry ripening process. Following the illumination, the composition of anthocyanins and other phenolic compounds was analysed at the mature ripening stage of fruits. All the three monochromatic light treatments had significant positive effect on the accumulation of total anthocyanins in ripe fruits compared to treatment with white light or plants kept in darkness. The elevated levels of anthocyanins were mainly due to a significant increase in the accumulation of delphinidin glycosides. A total of 33 anthocyanin compounds were detected in ripe bilberry fruits, of which six are novel in bilberry (cyanidin acetyl-3-O-galactose, malvidin acetyl-3-O-galactose, malvidin coumaroyl-3-O-galactose, malvidin coumaroyl-3-O-glucose, delphinidin coumaroyl-3-O-galactose, delphinidin coumaroyl-3-O-glucose). Our results indicate that the spectral composition of light during berry development has significant effect on the flavonoid composition of ripe bilberry fruits.
Grajeda-Iglesias, Claudia; Figueroa-Espinoza, Maria C; Barouh, Nathalie; Baréa, Bruno; Fernandes, Ana; de Freitas, Victor; Salas, Erika
The intense red-colored Hibiscus sabdariffa flowers are an inexpensive source of anthocyanins with potential to be used as natural, innocuous, and health-beneficial colorants. An anthocyanin-rich extract from hibiscus flowers was obtained by ultrasound-assisted extraction. By a single-step process fractionation using a Sep-Pak C18 cartridge, the main hibiscus anthocyanins, delphinidin-3-O-sambubioside (Dp-samb) and cyanidin-3-O-sambubioside (Cy-samb), were separated and then characterized via NMR and HPLC-ESIMS data. Since Dp-samb was the most abundant anthocyanin identified in the extract, its colorant properties were studied by the pH jumps method, which allowed the calculation of the single acid-base equilibrium (pK'a 2.92), the acidity (pKa 3.70), and the hydration constants (pKh 3.02). Moreover, by using size-exclusion chromatography, new cyanidin-derived anthocyanins (with three or more sugar units) were successfully identified and reported for the first time in the hibiscus extract.
Köchling, Joachim; Schmidt, Manuel; Rott, Yvonne; Sagner, Michael; Ungefroren, Hendrik; Wittig, Burghard; Henze, Günter
Chemotherapy and tyrosine kinase inhibitors provide high remission rates. However, prognosis of adult patients with Philadelphia chromosome-positive acute lymphoblastic leukaemia (Ph(+) ALL) still remains poor. Because most adults eventually relapse without allogeneic stem cell transplantation, which is not available for all patients, novel strategies are required for relapse prevention. As the integrity of the immune system is essential for the control of remaining leukaemia cells, we compared the efficacy of anthocyanins, imatinib and a DNA-based vaccine as non-immunosuppressant components with 6-mercaptopurine (6-MP) to control minimal residual disease in vitro and in vivo using different leukaemia cell lines and syngeneic mice. Proliferation of Ph(+) ALL was significantly better inhibited by anthocyanin-rich berry extract or imatinib compared with 6-MP. Although anthocyanins induced apoptosis in some leukaemia cell lines, the level of caspase-3, caspase-8 and caspase-9 was significantly lower compared with imatinib and 6-MP. When used as single components, anthocyanins and imatinib mesylate failed to eradicate pre-existing Ph(+) ALL in syngeneic mice, while 6-MP led to 10% and DNA vaccination to 56% survival. Intriguingly, only the combination of DNA vaccination with berry extract but not with the isolated anthocyanin, cyanidin-3-rutinoside or imatinib further increased leukaemia-free and overall survival, and 90% of lethally challenged mice survived. We suggest that induction and enhancement of a leukaemia-specific immunity by DNA vaccination and anthocyanin-rich berry extract can also decrease the relapse rate in patients with Ph(+) ALL. Furthermore, this approach may serve as strategy for maintenance therapy of other malignancies.
Xu, Zhi-Sheng; Feng, Kai; Que, Feng; Wang, Feng; Xiong, Ai-Sheng
Carrots are widely grown and enjoyed around the world. Purple carrots accumulate rich anthocyanins in the taproots, while orange, yellow, and red carrots accumulate rich carotenoids in the taproots. Our previous studies indicated that variation in the activity of regulatory genes may be responsible for variations in anthocyanin production among various carrot cultivars. In this study, an R2R3-type MYB gene, designated as DcMYB6, was isolated from a purple carrot cultivar. In a phylogenetic analysis, DcMYB6 was grouped into an anthocyanin biosynthesis-related MYB clade. Sequence analyses revealed that DcMYB6 contained the conserved bHLH-interaction motif and two atypical motifs of anthocyanin regulators. The expression pattern of DcMYB6 was correlated with anthocyanin production. DcMYB6 transcripts were detected at high levels in three purple carrot cultivars but at much lower levels in six non-purple carrot cultivars. Overexpression of DcMYB6 in Arabidopsis led to enhanced anthocyanin accumulation in both vegetative and reproductive tissues and upregulated transcript levels of all seven tested anthocyanin-related structural genes. Together, these results show that DcMYB6 is involved in regulating anthocyanin biosynthesis in purple carrots. Our results provide new insights into the regulation of anthocyanin synthesis in purple carrot cultivars. PMID:28345675
Podsędek, Anna; Koziołkiewicz, Maria
Red cabbage is, among different vegetables, one of the major sources of anthocyanins. In the present study an in vitro digestion method has been used to assay the influence of the physiological conditions in the stomach and small intestine, as well as faecal microflora on anthocyanins stability in red cabbage and anthocyanin-rich extract. The recovery of anthocyanins during in vitro gastrointestinal digestion was strongly influenced by food matrix. The results showed that other constituents present in cabbage enhanced the stability of anthocyanins during the digestion. The amount of anthocyanins (HPLC method) and antioxidant capacity (ABTS and FRAP assays) strongly decreased after pancreatic-bile digestion in both matrices but total phenolics content (Folin-Ciocalteu assay) in these digestions was higher than in initial samples. Incubation with human faecal microflora caused further decline in anthocyanins content. The results obtained suggest that intact anthocyanins in gastric and products of their decomposition in small and large intestine may be mainly responsible for the antioxidant activity and other physiological effects after consumption of red cabbage. PMID:24575407
Podsędek, Anna; Redzynia, Małgorzata; Klewicka, Elżbieta; Koziołkiewicz, Maria
Red cabbage is, among different vegetables, one of the major sources of anthocyanins. In the present study an in vitro digestion method has been used to assay the influence of the physiological conditions in the stomach and small intestine, as well as faecal microflora on anthocyanins stability in red cabbage and anthocyanin-rich extract. The recovery of anthocyanins during in vitro gastrointestinal digestion was strongly influenced by food matrix. The results showed that other constituents present in cabbage enhanced the stability of anthocyanins during the digestion. The amount of anthocyanins (HPLC method) and antioxidant capacity (ABTS and FRAP assays) strongly decreased after pancreatic-bile digestion in both matrices but total phenolics content (Folin-Ciocalteu assay) in these digestions was higher than in initial samples. Incubation with human faecal microflora caused further decline in anthocyanins content. The results obtained suggest that intact anthocyanins in gastric and products of their decomposition in small and large intestine may be mainly responsible for the antioxidant activity and other physiological effects after consumption of red cabbage.
Yousuf, Basharat; Gul, Khalid; Wani, Ali Abas; Singh, Preeti
Anthocyanins are one of the six subgroups of large and widespread group of plant constituents known as flavonoids. These are responsible for the bright and attractive orange, red, purple, and blue colors of most fruits, vegetables, flowers and some cereal grains. More than 600 structurally distinct anthocyanins have been identified in nature. Earlier, anthocyanins were only known for their coloring properties but now interest in anthocyanin pigments has intensified because of their possible health benefits as dietary antioxidants, which help to prevent neuronal diseases, cardiovascular illnesses, cancer, diabetes, inflammation, and many such others diseases. Ability of anthocyanins to counter oxidants makes them atherosclerosis fighters. Therefore, anthocyanin-rich foods may help to boost overall health by offering an array of nutrients. However, the incorporation of anthocyanins into food and medical products is a challenging task due to their low stability toward environmental conditions during processing and storage. Encapsulation seems to be an efficient way to introduce such compounds into these products. Encapsulating agents act as a protector coat against ambient adverse conditions such as light, humidity, and oxygen. Encapsulated bioactive compounds are easier to handle and offer improved stability. The main objective of this review is to explore health benefits of anthocyanins and their extraction, characterization, encapsulation, and delivery.
Trost, K; Golc-Wondra, A; Prosek, M; Milivojevic, L
Blueberry-aronia nectar is known as a rich source of anthocyanins, which are mostly destroyed during commercial storage of the product. The factors influencing the rate of degradation are connected to the oxygen protection offered by the packaging, as well as the type of anthocyanidin and the amount of glycosylated sugar. The current study was aimed to compare the stability of total anthocyanin between glass and carton packaging as well as to determine the stability of individual anthocyanin with respect to aglycone and glycosylated sugar. The degradation rate of total anthocyanin degradation rate was 22% higher in carton packaging than glass bottle. The ranking order of the stability of individual anthocyanin with respect to aglycone was as follows (from the most to least stable): cyanindin > peonidin > petunidin > malvidin = delphinidin. The ranking order of the stability of anthocyanins with respect to glycosylated sugars was as follows (from the most to least stable): glucose > galactose > arabinose. As individual anthocyanins have different degradation rates this study can be used to determine the most stable natural colorant and the most sensitive antioxidant among the anthocyanins tested.
Francis, F J
Interest in food colorants as shown by the number of patents has doubled in recent years with natural pigments outnumbering synthetics by five to one. The natural colorant area can be subdivided into anthocyanins, betalains, chlorophylls, carotenoids, flavonoids, polyphenols, Monascus, hemes, quinones, biliproteins, safflower, turmeric, and miscellaneous. All involve different groups of chemical compounds which may be used directly as colorants, or may be chemically modified to produce different hues or increased stability. All usually involve a method of collection, extraction, purification, possibly stabilization, and formulation. A variety of hues can be obtained ranging from green through yellow, orange, red, blue, and violet, depending on the source of colorant. Similarly, water or oil-soluble formulations can be prepared depending on the type of colorant.
Craker, L. E.; Standley, L. A.; Starbuck, M. J.
Light-induced anthocyanin synthesis in Sorghum vulgare L. seedlings was both promoted and inhibited by ethylene treatment. The rate of anthocyanin formation in sorghum tissue was dependent upon the time of ethylene treatment in relation to light exposure and the stage of the anthocyanin synthesis process. Those plants receiving ethylene treatment during the early lag phase of anthocyanin synthesis had higher anthocyanin content at 24 hours than control plants receiving no ethylene treatment. Plants receiving ethylene treatment after the lag phase had lower anthocyanin content at 24 hours than control plants receiving no ethylene treatment. PMID:16657796
Accumulation of molybdenum in Brassica was recently found to be correlated with anthocyanin content, involving the formation of a blue complex. Here the role of anthocyanins in tungsten sequestration was investigated using three species of Brassica: B. rapa (cv. Fast plants), B. juncea (Indian mustard) and B. oleracea (red cabbage). Seedlings of B. rapa and B. juncea turned blue when supplied with colourless tungstate. The blue compound co-localized with anthocyanins in the peripheral cell layers, and the degree of blueness was correlated with anthocyanin content. The direct involvement of anthocyanins in the blue coloration was evident when purified anthocyanins showed a colour change from pink to blue in vitro upon addition of tungstate, over a wide pH range. Anthocyanin production was upregulated 3-fold by W in B. juncea, possibly reflecting a function for anthocyanins in W tolerance or sequestration. The presence of anthocyanins facilitated W accumulation in B. rapa: anthocyanin-containing seedlings accumulated 3-fold more W than an anthocyaninless mutant. There was no correlation between anthocyanin content and W tolerance under these conditions. The nature of the interaction between anthocyanins and tungstate was investigated. X-ray absorption spectroscopy showed no change in the local chemical environment of Wupon uptake of tungstate by the plant; HPLC analysis of purified anthocyanin with or without tungstate showed no peak shift after metal treatment.
Krga, Irena; Monfoulet, Laurent-Emmanuel; Konic-Ristic, Aleksandra; Mercier, Sylvie; Glibetic, Maria; Morand, Christine; Milenkovic, Dragan
An increasing number of evidence suggests a protective role of dietary anthocyanins against cardiovascular diseases. Anthocyanins' extensive metabolism indicates that their metabolites could be responsible for the protective effects associated with consumption of anthocyanin-rich foods. The aim of this work was to investigate the effect of plasma anthocyanins and their metabolites on the adhesion of monocytes to TNFα-activated endothelial cells and on the expression of genes encoding cell adhesion molecules. Human umbilical vein endothelial cells (HUVECs) were exposed to circulating anthocyanins: cyanidin-3-arabinoside, cyanidin-3-galactoside, cyanidin-3-glucoside, delphinidin-3-glucoside, peonidin-3-glucoside, anthocyanin degradation product: 4-hydroxybenzaldehyde, or to their gut metabolites: protocatechuic, vanillic, ferulic and hippuric acid, at physiologically-relevant concentrations (0.1-2 μM) and time of exposure. Both anthocyanins and gut metabolites decreased the adhesion of monocytes to HUVECs, with a magnitude ranging from 18.1% to 47%. The mixture of anthocyanins and that of gut metabolites also reduced monocyte adhesion. However, no significant effect on the expression of genes encoding E-selectin, ICAM1 and VCAM1 was observed, suggesting that other molecular targets are involved in the observed effect. In conclusion, this study showed the potency of anthocyanins and their gut metabolites to modulate the adhesion of monocytes to endothelial cells, the initial step in atherosclerosis development, under physiologically-relevant conditions.
Su, Nana; Lu, Yanwu; Wu, Qi; Liu, Yuanyuan; Xia, Yan; Xia, Kai; Cui, Jin
Raphanus sativus L. cv. Yanghua sprouts are rich in health-promoting anthocyanins; thus hypocotyls show a red color under light. In this study, effects of UV-B irradiation at 5 W m(-2) on anthocyanin biosynthesis in the hypocotyls of radish sprouts were investigated. Anthocyanins began to accumulate rapidly from 24 h irradiation and increased continuously until 48 h, showing a similar pattern to phenylalanine ammonia lyase (PAL) activity, with a correlation coefficient of 0.804. The expression of DFR and ANS paralleled the upward trend in anthocyanin accumulation, while CHS, CHI and F3H were upregulated before accumulation. When sprouts were moved into the dark from UV-B, the anthocyanin accumulation did not stop immediately. By contrast, anthocyanin accumulated continuously for more than 12 h in the dark, which was further supported by the significantly higher PAL activity monitored at 24 h after irradiation. Similarly, the transcript levels of anthocyanin biosynthesis-related genes were much higher over 6 h after 12 h UV-B irradiation. UV-B-induced anthocyanin accumulation continues in the dark after irradiation, which was supported by unfading PAL activity and high levels of biosynthesis-related genes. This will provide evidence to produce high-quality sprouts with more anthocyanins but less energy wastage in practice. © 2015 Society of Chemical Industry.
Wallace, Taylor C.
Anthocyanins are a group of abundant and widely consumed flavonoid constituents that occur ubiquitously in the plant kingdom, providing the bright red-orange to blue-violet colors present in many fruit- and vegetable-based food products. Their intake has been estimated to be up to 9-fold higher than that of other dietary flavonoids. Anthocyanins have become increasingly important to the food industry as their use as natural alternatives to artificial colors has become widespread and knowledge of their health-promoting properties has become more evident. Epidemiological studies suggest that increased consumption of anthocyanins lowers the risk of cardiovascular disease (CVD), the most common cause of mortality among men and women. Anthocyanins frequently interact with other phytochemicals, exhibiting synergistic biological effects but making contributions from individual components difficult to decipher. Over the past 2 decades, many peer-reviewed publications have demonstrated that in addition to their noted in vitro antioxidant activity, anthocyanins may regulate different signaling pathways involved in the development of CVD. This review summarizes the latest developments on the bioavailability/bioactivity and CVD preventative activities of anthocyanins, including results from in vitro cell culture and in vivo animal model systems as related to their multiple proposed mechanisms of action. Limited yet promising data from epidemiological studies and human clinical trials are also presented. Future studies aimed at enhancing the absorption of anthocyanins and characterizing their metabolic and/or breakdown products are necessary to ultimately evaluate their use for protection/prevention against the development of CVD. PMID:22211184
Cai, Zhan; Qu, Ziqian; Lan, Yu; Zhao, Shujuan; Ma, Xiaohua; Wan, Qiang; Jing, Pu; Li, Pingfan
Purple sweet potatoes (PSPs) are rich in anthocyanins. In this study, we investigated the extraction efficiency of anthocyanins from PSPs using conventional extraction (CE), ultrasound-assisted extraction (UAE), and accelerated-solvent extraction (ASE). Additionally, the effects of these extraction methods on antioxidant activity and anthocyanin composition of PSP extracts were evaluated. In order of decreasing extraction efficiency, the extraction methods were ASE>UAE>CE for anthocyanins (218-244 mg/100 g DW) and CE>UAE>ASE for total phenolics (631-955 mg/100 g DW) and flavonoids (28-40 mg/100 g DW). Antioxidant activities of PSP extracts were CE≈UAE>ASE for ORAC (766-1091 mg TE/100 g DW) and ASE>CE≈UAE for FRAP (1299-1705 mg TE/100 g DW). Twelve anthocyanins were identified. ASE extracts contained more diacyl anthocyanins and less nonacyl and monoacyl anthocyanins than CE and ASE extracts (P<0.05). Copyright © 2015 Elsevier Ltd. All rights reserved.
The color of red cabbage is due to the accumulation of large quantity of anthocyanins. To investigate the general regulatory control of anthocyanin production in red cabbages, the expression of anthocyanin biosynthetic genes and regulators from eight commercial cultivars was examined. While the four...
Zhang, Yang; Butelli, Eugenio; Martin, Cathie
Anthocyanins are water-soluble pigments giving the red, purple and blue colours of many flowers and fruit. In addition to their physiological roles in plants, to attract pollinators and seed dispersers, dietary anthocyanins are associated with protection against certain cancers, cardiovascular diseases and other chronic human disorders. Enhanced supplies of pure anthocyanins would service the demands of research to investigate these health-promoting effects and would also prove a valuable resource for the colourants and cosmetic industries to investigate the effects of chemical modifications, co-pigments, and pH on colour and stability for developing new plant sources of natural colourants, and new natural colours. Copyright © 2014. Published by Elsevier Ltd.
Hu, Yijie; Deng, Liqing; Chen, Jinwu; Zhou, Siyu; Liu, Shuang; Fu, Yufan; Yang, Chunxian; Liao, Zhihua; Chen, Min
Purple sweet potato (Ipomoea batatas L.) is rich in anthocyanin pigments, which are valuable constituents of the human diet. Techniques to identify and quantify anthocyanins and their antioxidant potential are desirable for cultivar selection and breeding. In this study, we performed a quantitative and qualitative chemical analysis of 30 purple sweet potato (PSP) cultivars, using various assays to measure reducing power radical-scavenging activities, and linoleic acid autoxidation inhibition activity. Grey relational analysis (GRA) was applied to establish relationships between the antioxidant activities and the chemical fingerprints, in order to identify key bioactive compounds. The results indicated that four peonidin-based anthocyanins and three cyanidin-based anthocyanins make significant contributions to antioxidant activity. We conclude that the analytical pipeline described here represents an effective method to evaluate the antioxidant potential of, and the contributing compounds present in, PSP cultivars. This approach may be used to guide future breeding strategies. Copyright © 2015. Published by Elsevier Ltd.
The type and amount of anthocyanins in raspberries, and other small fruits, has recently received increased attention. Black raspberry (Rubus occidentalis L.), in particular, has long been recognized as a rich source of anthocyanins and has been the focus of many recent studies examining their poten...
Anthocyanins are a group of water-soluble pigments that confer the blue, purple, and red color to many fruits. Anthocyanin-rich fruits can be divided into three groups based on the types of aglycones of their anthocyanins: pelargonidin group, cyanidin/peonidin group, and multiple anthocyanidins group. Some fruits contain a major anthocyanin type and can serve as useful research tools. Cyanidin glycosides and peonidin glycosides can be metabolically converted to each other by methylation and demethylation. Both cyanidin and peonidin glycosides can be metabolized to protocatechuic acid and vanillic acid. Pelargonidin-3-glucoside is metabolized to 4-hydroxybenoic acid. On the other hand, phenolic acid metabolites of delphinidin, malvidin, and petunidin glycosides are unstable and can be further fragmented into smaller molecules. A literature review indicates berries with higher cyanidin content, such as black raspberries, chokeberries, and bilberries are more likely to produce an antiinflammatory effect. This observation seems to be consistent with the hypothesis that one or more stable phenolic acid metabolites contribute to the antiinflammatory effects of anthocyanin-rich fruits. More studies are needed before we can conclude that fruits rich in cyanidin, peonidin, or pelargonidin glycosides have better antiinflammatory effects. Additionally, fruit polyphenols other than anthocyanins could contribute to their antiinflammatory effects. Furthermore, blueberries could exert their health effects with other mechanisms such as improving intestinal microbiota composition. In summary, this classification system can facilitate our understanding of the absorption and metabolic processes of anthocyanins and the health effects of different fruits. Crown Copyright © 2015. Published by Elsevier Inc. All rights reserved.
Guo, Ning; Cheng, Feng; Wu, Jian; Liu, Bo; Zheng, Shuning; Liang, Jianli; Wang, Xiaowu
Anthocyanins are a group of flavonoid compounds. As a group of important secondary metabolites, they perform several key biological functions in plants. Anthocyanins also play beneficial health roles as potentially protective factors against cancer and heart disease. To elucidate the anthocyanin biosynthetic pathway in Brassica rapa, we conducted comparative genomic analyses between Arabidopsis thaliana and B. rapa on a genome-wide level. In total, we identified 73 genes in B. rapa as orthologs of 41 anthocyanin biosynthetic genes in A. thaliana. In B. rapa, the anthocyanin biosynthetic genes (ABGs) have expanded and most genes exist in more than one copy. The anthocyanin biosynthetic structural genes have expanded through whole genome and tandem duplication in B. rapa. More structural genes located upstream of the anthocyanin biosynthetic pathway have been retained than downstream. More negative regulatory genes are retained in the anthocyanin biosynthesis regulatory system of B. rapa. These results will promote an understanding of the genetic mechanism of anthocyanin biosynthesis, as well as help the improvement of the nutritional quality of B. rapa through the breeding of high anthocyanin content varieties.
Mane, Shon; Bremner, David H; Tziboula-Clarke, Athina; Lemos, M Adília
This study examined anthocyanin extraction using the application of ultrasound to raw freeze dried, microwaved and raw sliced Purple Majesty potato, a new pigmented potato variety rich in anthocyanins. A 20 kHz probe was used for the sonication at 3 different amplitudes (30%, 50% and 70%) and ethanol in water at different ratios (50:50 and 70:30 v/v) was used for the extraction. Anthocyanin extraction from raw freeze dried purple potato was optimal at an ethanol:water ratio (70:30; v/v) after 5 min of ultrasonication, while the least amount of anthocyanins was extracted from raw sliced potatoes. The application of microwaves (as a pre-treatment) before the UAE resulted in an increase in the amount of anthocyanins extracted and a decrease in the amount of solvent used. Analysis of variance showed that potato form, ultrasonication time, ultrasonication amplitude and solvent ratio as well as two and three way interactions between some of these factors had a very significant effect (p<0.000) on the amount of anthocyanins extracted. Copyright © 2015 Elsevier B.V. All rights reserved.
Viskelis, P; Rubinskiene, M; Jasutiene, I; Sarkinas, A; Daubaras, R; Cesoniene, L
Amounts of total phenolics, anthocyanins, and ascorbic acid in 4 American cranberry varieties harvested at 4 stages of maturity were measured. The larger amount of phenolic compounds was found in berries of "Black Veil" cultivar (504 mg/100 g) at II stage of maturity. Significantly larger amounts of anthocyanins were determined in the overripe berries of the cultivars "Ben Lear" and "Black Veil." The amount of ascorbic acid in berries increased during ripening from I to III stage, and slightly decreased in the overripe berries. The biggest quantities of ascorbic acid were found in the ripe berries of "Ben Lear" cultivar (15.8 mg/100 g). The distribution of anthocyanins pigments was determined by HPLC-UV/MS in mature berries. The composition of individual anthocyanins in berries was quite similar in all the studied cranberry cultivars. While skins of cranberries are rich in anthocyanins and other phenolic compounds, the extracts of the by-products of cranberries juice-berry cakes, were analyzed and obtained results were compared with the properties of extracts made from whole berries. The anthocyanins and total phenolics content, radical scavenging activity, antimicrobial activity of the whole berries, and their press cakes extracts were measured. All investigated extracts from berries and their press cakes showed good radical scavenging activity and revealed antimicrobial properties. It was found that Bacillus cereus (ATCC 10876) and Micrococcus luteus (ATCC 9341) were the most sensitive among 10 tested Gram-negative and Gram-positive bacteria.
Yao, Lijuan; Zhang, Na; Wang, Chenbiao; Wang, Chunhong
Powdered bilberry extract (United States Pharmacopoeia, USP35-NF30), which is prepared from ripe bilberry fruits (Vaccinium myrtillus L.), is the main ingredient of drugs alleviating visual fatigue and diabetic retinopathy because of the rich anthocyanins (purity of 36%). In this study, a method based on a macroporous polymeric adsorbent was established to obtain anthocyanin compounds from bilberry, in which the purity of the anthocyanins was improved to 96%, conducive to further pharmacological research and improvement of the efficiency of the drug. On the basis of the structure of anthocyanins, we designed a series of macroporous polymeric adsorbents based on the copolymerization of divinylbenzene (DVB) and ethylene glycol dimethyl acrylate (EGDMA). In this situation, EGDMA not only regulated the polarity of the adsorbent but also acted as the cross-linking agent to ensure the matrix structure of the adsorbent, which had a high specific surface area and could provide more interaction sites during adsorption with anthocyanins. Among the synthesized polymeric adsorbents with different contents of EGDMA, the one with 20% EGDMA content (DE-20) was demonstrated to exhibit optimal adsorption capacity and selectivity to anthocyanins compared to various commercial adsorbents through static adsorption and desorption experiments. In addition, the optimum condition of the dynamic adsorption-desorption experiment was further explored. The results indicated that the purity of anthocyanins after rinsing with 20% ethanol was determined to be approximately 96% at a desorption ratio of 83%, which was clearly higher than that in powdered bilberry extract. The established separation and purification method of anthocyanins with high purity is expected to be applied in industrial production.
Wang, Liang-Zai; Hu, Yan-Bo; Zhang, Hui-Hui; Xu, Nan; Zhang, Xiu-Li; Sun, Guang-Yu
Anthocyanin is widely distributed in plant organs such as root, stem, leaf, flower and fruit, being a kind of secondary metabolites generated in plant morphogenesis or for stress response. Leaf anthocyanin has special chemical structure and spectral properties, playing important roles in plant photoprotection, and becomes a hotspot in plant photosynthetic physiological ecology. This paper summarized the recent research progress in the effects of leaf anthocyanin on plant photosynthesis, including the distribution of leaf anthocyanin, its spectral properties, and its relationships with photosynthetic pigments, with the focus on the potential mechanisms of anthocyanins photoprotection, including light absorption, antioxidation, and osmotic regulation. The further research directions on the effects of leaf anthocyanin on photoprotection were proposed.
Vauzour, David; Tejera, Noemi; O'Neill, Colette; Booz, Valeria; Jude, Baptiste; Wolf, Insa M.A.; Rigby, Neil; Silvan, Jose Manuel; Curtis, Peter J.; Cassidy, Aedin; de Pascual-Teresa, Sonia; Rimbach, Gerald; Minihane, Anne Marie
Increased tissue status of the long-chain n-3 polyunsaturated fatty acids (LC n-3 PUFA), eicosapentaenoic (EPA) and docosahexaenoic acid (DHA) is associated with cardiovascular and cognitive benefits. Limited epidemiological and animal data suggest that flavonoids, and specifically anthocyanins, may increase EPA and DHA levels, potentially by increasing their synthesis from the shorter-chain n-3 PUFA, α-linolenic acid. Using complimentary cell, rodent and human studies we investigated the impact of anthocyanins and anthocyanin-rich foods/extracts on plasma and tissue EPA and DHA levels and on the expression of fatty acid desaturase 2 (FADS2), which represents the rate limiting enzymes in EPA and DHA synthesis. In experiment 1, rats were fed a standard diet containing either palm oil or rapeseed oil supplemented with pure anthocyanins for 8 weeks. Retrospective fatty acid analysis was conducted on plasma samples collected from a human randomized controlled trial where participants consumed an elderberry extract for 12 weeks (experiment 2). HepG2 cells were cultured with α-linolenic acid with or without select anthocyanins and their in vivo metabolites for 24 h and 48 h (experiment 3). The fatty acid composition of the cell membranes, plasma and liver tissues were analyzed by gas chromatography. Anthocyanins and anthocyanin-rich food intake had no significant impact on EPA or DHA status or FADS2 gene expression in any model system. These data indicate little impact of dietary anthocyanins on n-3 PUFA distribution and suggest that the increasingly recognized benefits of anthocyanins are unlikely to be the result of a beneficial impact on tissue fatty acid status. PMID:25573539
Cahliková, Lucie; Ali, Badreldin H; Havliková, Lucie; Ločárek, Mirek; Siatka, Tomáš; Opletal, Lubomir; Blunden, Gerald
Extracts of the calyces of Hibiscus sabdariffa are widely used in folk medicine to combat many illnesses. The active constituents of the extracts have been shown on several occasions to be anthocyanins. In our current studies the biological activities of an extract of H. sabdariffa calyces purchased in Oman, but grown in Sudan, are being compared with those of the anthocyanins isolated from them, and, for this, the anthocyanin profile of the extract needed to be ascertained. Although several anthocyanins were detected by UHPLC-ESI-MS/MS, delphinidin-3-sambubioside (major) and cyanidin-3-sambubioside were predominant.
Wallace, T C; Giusti, M M
Anthocyanins are of interest to the food industry because of their antioxidant power, attractive color, and stability in high acid foods. Powder from the Peruvian berry Berberis boliviana Lechler, rich in nonacylated anthocyanins (7% to 8% dry weight), was incorporated into yogurt samples containing 3 different fat levels. Color (CIE L, a, b, chroma, and hue angle), pigment (monomeric anthocyanin and polymeric color), and total phenolics were monitored over 8 wk of storage and compared to yogurt treatments containing purple carrot acylated anthocyanins, red beet betalaines, or FD&C Red nr 40. Anthocyanin profiles were analyzed by HPLC coupled to photodiode array and mass detectors. Color of yogurt containing B. boliviana anthocyanins at 20 mg cyanidin-3-glucoside (cy-3-glu) equivalents/100 g yogurt (L*= 65, chroma = 14, and hue angle = 335 degrees ) was similar to commercial blueberry yogurt (L*= 65, chroma = 10.5, and hue angle = 341 degrees ). High color, pigment, and phenolic stability were observed in yogurts colored with B. boliviana, independent of the fat matrix. Acylated anthocyanins from purple carrot extracts exhibited increased stability with higher fat content. Anthocyanin degradation followed 1st-order kinetics. Pigment half-lives were 125 and 104 d for nonacylated anthocyanins at 10 and 20 mg cy-3-glu equivalents/100 g yogurt and 550.2, 232.6, and 128.9 d for acylated anthocyanins at 20 mg of cy-3-glu equivalents/100 g of 4%, 2%, and 0% fat yogurt. Addition of B. boliviana whole berry powder to yogurt matrices produced an attractive, stable anthocyanin-rich product, eliminating the need for industrial colorant extraction.
Ai, Trinh Ngoc; Naing, Aung Htay; Arun, Muthukrishnan; Lim, Sun-Hyung; Kim, Chang Kil
The effects of three different sucrose concentrations on plant growth and anthocyanin accumulation were examined in non-transgenic (NT) and transgenic (T2) specimens of the Petunia hybrida cultivar 'Mirage rose' that carried the anthocyanin regulatory transcription factors B-Peru+mPAP1 or RsMYB1. Anthocyanin accumulation was not observed in NT plants in any treatments, whereas a range of anthocyanin accumulation was observed in transgenic plants. The anthocyanin content detected in transgenic plants expressing the anthocyanin regulatory transcription factors (B-Peru+mPAP1 or RsMYB1) was higher than that in NT plants. In addition, increasing sucrose concentration strongly enhanced anthocyanin content as shown by quantitative real-time polymerase chain reaction (qRT-PCR) analysis, wherein increased concentrations of sucrose enhanced transcript levels of the transcription factors that are responsible for the induction of biosynthetic genes involved in anthocyanin synthesis; this pattern was not observed in NT plants. In addition, sucrose affected plant growth, although the effects were different between NT and transgenic plants. Taken together, the application of sucrose could enhance anthocyanin production in vegetative tissue of transgenic Petunia carrying anthocyanin regulatory transcription factors, and this study provides insights about interactive effects of sucrose and transcription factors in anthocyanin biosynthesis in the transgenic plant. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.
Suzuki, Tatsuro; Kim, Sun-Ju; Mohamed, Zaidul Islam Sarker; Mukasa, Yuji; Takigawa, Shigenobu; Matsuura-Endo, Chie; Yamauchi, Hiroaki; Hashimoto, Naoto; Noda, Takahiro; Saito, Tatsuya
The anthocyanin profiles and variety/breeding-line differences of anthocyanin concentrations in petals of common buckwheat flowers have been studied. Four anthocyanins, cyanidin 3-O-glucoside, cyanidin 3-O-rutinoside, cyanidin 3-O-rhamnoside, and cyanidin 3-O-galactosyl-rhamnoside were isolated from the petals of common buckwheat (Fagopyrum esculentum Moench), separated using high performance liquid chromatography and identified using reversed-phase liquid chromatography-electrospray ionization-tandem mass spectrometry techniques. In every variety/breeding line tested, cyanidin 3-O-rutinoside was detected as the major anthocyanin and the next is cyanidin 3-O-glucoside whereas cyanidin 3-O-rhamnoside and cyanidin 3-O-galactosyl-rhamnoside were trace or not detectable in white and pink flowered buckwheat. Of all the varieties/breeding lines tested, Gan-Chao, a Chinese variety, contained the highest amount of anthocyanins. The largest part of cyanidin moiety was presented as a proanthocyanidin form (PAs-Cy). Anthocyanins and PAs-Cy in petals were increased along with increase of flower development stages. Therefore, fully developed petals of red flowered buckwheat, especially Gan-Chao, are promising as a new anthocyanin-rich material for food processing.
Devi, P. Suganya; Kumar, M. Saravana; Das, S. Mohan
There is increasing interest in natural food colorants like carotenoids and anthocyanins with functional properties. Red sorghum bran is known as a rich source for anthocyanins. The anthocyanin contents extracted from red sorghum bran were evaluated by biochemical analysis. Among the three solvent system used, the acidified methanol extract showed a highest anthocyanin content (4.7 mg/g of sorghum bran) followed by methanol (1.95 mg/g) and acetone (1 mg/g). Similarly, the highest total flavonoids (143 mg/g) and total phenolic contents (0.93 mg/g) were obtained in acidified methanol extracts than methanol and acetone extracts. To study the health benefits of anthocyanin from red sorghum bran, the total antioxidant activity was evaluated by biochemical and molecular methods. The highest antioxidant activity was observed in acidified methanol extracts of anthocyanin in dose-dependent manner. The antioxidant activity of the red sorghum bran was directly related to the total anthocyanin found in red sorghum bran. PMID:22400119
Hager, Tiffany J; Howard, Luke R; Prior, Ronald L
Blackberries are a rich source of polyphenolics, particularly anthocyanins, that may contribute to the reduced risk of chronic disease; however, as with most berries, the fresh fruit are only seasonally available. With most of the blackberries consumed as frozen or in thermally processed forms after long-term storage, the purpose of this study was to evaluate the effects of processing and 6 months of storage on the anthocyanins and antioxidant capacity of blackberries that were individually quick-frozen (IQF), canned-in-syrup, canned-in-water, pureed, and juiced (clarified and nonclarified). Monomeric anthocyanins, percent polymeric color, and antioxidant capacity by oxygen radical absorbance capacity (ORAC FL) and photochemiluminescence (PCL) were determined postprocessing (1 day) and after 1, 3, and 6 months of storage. Processing resulted in increases in polymeric color values (up to 7%) and losses in monomeric anthocyanins (up to 65%). For most products, processing also resulted in losses in antioxidant capacity (by ORAC FL and PCL). Storage at 25 degrees C of all processed products resulted in dramatic losses in monomeric anthocyanins with as much as 75% losses of anthocyanins throughout storage, which coincided with marked increases of percent polymeric color values of these products over 6 months of storage. There were no changes in ORAC FL or PCL for processed products throughout long-term storage. No significant changes in antioxidant capacity or anthocyanin content were observed in IQF fruit during long-term storage at -20 degrees C.
Ribnicky, David M.; Roopchand, Diana E.; Oren, Andrew; Grace, Mary; Poulev, Alexander; Lila, Mary Ann; Havenaar, Robert; Raskin, Ilya
The TNO intestinal model (TIM-1) of the human upper gastrointestinal tract was used to compare intestinal absorption/bioaccessibility of blueberry anthocyanins under different digestive conditions. Blueberry polyphenol-rich extract was delivered to TIM-1 in the absence or presence of a high-fat meal. HPLC analysis of seventeen anthocyanins showed that delphinidin-3-glucoside, delphinidin-3-galactoside, delphinidin-3-arabinoside and petunidin-3-arabinoside were twice as bioaccessible in fed state, whilst delphinidin-3-(6″-acetoyl)-glucoside and malvidin-3-arabinoside were twice as bioaccessible under fasted conditions, suggesting lipid-rich matrices selectively effect anthocyanin bioaccessibility. TIM-1 was fed blueberry juice (BBJ) or blueberry polyphenol-enriched defatted soybean flour (BB-DSF) containing equivalent amounts of free or DSF-sorbed anthocyanins, respectively. Anthocyanin bioaccessibility from BB-DSF (36.0 ± 10.4) was numerically, but not significantly, greater than that from BBJ (26.3 ± 10.3). Ileal efflux samples collected after digestion of BB-DSF contained 2.8-fold more anthocyanins than same from BBJ, suggesting that protein-rich DSF protects anthocyanins during transit through upper digestive tract for subsequent colonic delivery/metabolism. PMID:24001852
Ribnicky, David M; Roopchand, Diana E; Oren, Andrew; Grace, Mary; Poulev, Alexander; Lila, Mary Ann; Havenaar, Robert; Raskin, Ilya
The TNO intestinal model (TIM-1) of the human upper gastrointestinal tract was used to compare intestinal absorption/bioaccessibility of blueberry anthocyanins under different digestive conditions. Blueberry polyphenol-rich extract was delivered to TIM-1 in the absence or presence of a high-fat meal. HPLC analysis of seventeen anthocyanins showed that delphinidin-3-glucoside, delphinidin-3-galactoside, delphinidin-3-arabinoside and petunidin-3-arabinoside were twice as bioaccessible in fed state, whilst delphinidin-3-(6″-acetoyl)-glucoside and malvidin-3-arabinoside were twice as bioaccessible under fasted conditions, suggesting lipid-rich matrices selectively effect anthocyanin bioaccessibility. TIM-1 was fed blueberry juice (BBJ) or blueberry polyphenol-enriched defatted soybean flour (BB-DSF) containing equivalent amounts of free or DSF-sorbed anthocyanins, respectively. Anthocyanin bioaccessibility from BB-DSF (36.0±10.4) was numerically, but not significantly, greater than that from BBJ (26.3±10.3). Ileal efflux samples collected after digestion of BB-DSF contained 2.8-fold more anthocyanins than same from BBJ, suggesting that protein-rich DSF protects anthocyanins during transit through upper digestive tract for subsequent colonic delivery/metabolism. Copyright © 2013 Elsevier Ltd. All rights reserved.
Grajeda-Iglesias, Claudia; Salas, Erika; Barouh, Nathalie; Baréa, Bruno; Figueroa-Espinoza, Maria Cruz
Hibiscus sabdariffa flowers represent an interesting source of anthocyanins, one of the most important plant pigments, which are responsible of the intense red color of the calyces, and have potential as natural colorants for food applications. Nevertheless, anthocyanins are highly hydrosoluble and unstable compounds. On this basis, the aim of this work was to increase the lipophilicity of the hibiscus anthocyanins by lipophilization, in order to obtain amphiphilic colorants, which could be easily incorporated in lipid-rich food matrices. Octanoyl derivatives of delphinidin-3-O-sambubioside and cyanidin-3-O-sambubioside were chemically obtained for the first time, and characterized by means of HPLC-ESI-MS data. Copyright © 2017. Published by Elsevier Ltd.
Xu, Jin; Mojsoska, Biljana
Polyphenols comprise a diverse group of molecules with antioxidative and anti-inflammatory activities. To compare the antioxidative and anti-inflammatory capacity of Aronia melanocarpa berries (chokeberries), recognized for their high content of anthocyanins, a noncytotoxic isolation method was developed to obtain high-purity anthocyanins in the extract. The antioxidative activity of the extract, the anthocyanin-rich fraction (AF) was determined by 1,1-diphenyl-2-picrylhydrazyl radical and ferric-reducing ability of plasma along with resveratrol as a reference. The immunomodulation properties were assessed in lipopolysaccharide (LPS)-stimulated human monocytes mono mac 6. The isolated AF, containing six different anthocyanins, exhibited a stronger antioxidative capacity compared to resveratrol. Resveratrol enhanced tumor necrosis factor-α and reduced interleukin-10 (IL-10) production by LPS, whereas AF only had a slight effect in reducing IL-10. These results demonstrated that there was no major relationship between the antioxidative effect and immunomodulation capacities of AF and resveratrol. The immunomodulatory activity of the extract is associated with bioactive compounds in Aronia other than its anthocyanins.
Zhu, Yongjian; Bo, Yacong; Wang, Xi; Lu, Wenjie; Wang, Xule; Han, Zhanying; Qiu, Chunguang
Abstract The findings of clinical studies concerning the association between anthocyanins supplementation and blood pressure (BP) are inconsistent. In order to provide a more precise estimate of the overall effect of anthocyanins on systolic blood pressure (SBP) and diastolic blood pressure (DBP), we conducted a meta-analysis of clinical trials about anthocyanins supplementation and BP. PubMed, Web of Science, Wanfang Database, and China National Knowledge Infrastructure (CNKI) (until October 2015) were searched to identify potential studies with information on anthocyanins extract supplementation and arterial BP. The weighted mean difference (WMD) and 95% confidence interval (CI) were used as a summary statistic. Net changes in SBP and DBP between anthocyanins supplementation and placebo groups were calculated by subtracting the values at end of follow-up from those at baseline. Meta regression was used to explore the potential moderators of effect size. The publication bias was assessed using Begger's Funnel plots and Egger's tests; P < 0.05 was considered to be statistically significant. Finally, 6 clinical studies with 472 participants for the effect of anthocyanins consumption on BP were included in the present meta-analysis. There is no significant effect on either SBP (WMD: 1.15 mm Hg, 95% CI: −3.17 to 5.47, I2 = 56%) or DBP (WMD: 1.06 mm Hg, 95% CI: −0.71 to 2.83, I2 = 0%) following supplementation with anthocyanins. In summary, results from this meta-analysis do not favor any clinical efficacy of supplementation with anthocyanins in improving blood pressure. Further well-designed large randomized controlled trials (RCTs) with long follow-up period are needed to verify the association of anthocyanins supplementation and blood pressure. PMID:27082604
Xu, Zhi-Sheng; Huang, Ying; Wang, Feng; Song, Xiong; Wang, Guang-Long; Xiong, Ai-Sheng
Carrots (Daucus carota L.) are among the 10 most economically important vegetable crops grown worldwide. Purple carrot cultivars accumulate rich cyanidin-based anthocyanins in a light-independent manner in their taproots whereas other carrot color types do not. Anthocyanins are important secondary metabolites in plants, protecting them from damage caused by strong light, heavy metals, and pathogens. Furthermore, they are important nutrients for human health. Molecular mechanisms underlying anthocyanin accumulation in purple carrot cultivars and loss of anthocyanin production in non-purple carrot cultivars remain unknown. The taproots of the three purple carrot cultivars were rich in anthocyanin, and levels increased during development. Conversely, the six non-purple carrot cultivars failed to accumulate anthocyanins in the underground part of taproots. Six novel structural genes, CA4H1, CA4H2, 4CL1, 4CL2, CHI1, and F3'H1, were isolated from purple carrots. The expression profiles of these genes, together with other structural genes known to be involved in anthocyanin biosynthesis, were analyzed in three purple and six non-purple carrot cultivars at the 60-day-old stage. PAL3/PAL4, CA4H1, and 4CL1 expression levels were higher in purple than in non-purple carrot cultivars. Expression of CHS1, CHI1, F3H1, F3'H1, DFR1, and LDOX1/LDOX2 was highly correlated with the presence of anthocyanin as these genes were highly expressed in purple carrot taproots but not or scarcely expressed in non-purple carrot taproots. This study isolated six novel structural genes involved in anthocyanin biosynthesis in carrots. Among the 13 analyzed structural genes, PAL3/PAL4, CA4H1, 4CL1, CHS1, CHI1, F3H1, F3'H1, DFR1, and LDOX1/LDOX2 may participate in anthocyanin biosynthesis in the taproots of purple carrot cultivars. CHS1, CHI1, F3H1, F3'H1, DFR1, and LDOX1/LDOX2 may lead to loss of light-independent anthocyanin production in orange and yellow carrots. These results suggest that
The types of anthocyanins occurring in grapes, wines, and juices are described and their distribution documented. Recent work on the evaluation of red wine color during storage and aging is reviewed. Molecular interactions between anthocyanins and some of the other red wine molecules are shown to be associated with development of new pigments whose formation explains the subtle color changes and stabilization occurring on aging of red wines. A detailed description of the recovery of anthocyanins from grape pomace and production of natural red colorants is also given.
Bunea, Andrea; Rugină, Dumitriţa; Sconţa, Zoriţa; Pop, Raluca M; Pintea, Adela; Socaciu, Carmen; Tăbăran, Flaviu; Grootaert, Charlotte; Struijs, Karin; VanCamp, John
Blueberry consumption is associated with health benefits contributing to a reduced risk for cardiovascular disease, diabetes and cancer. The aim of this study was to determine the anthocyanin profile of blueberry extracts and to evaluate their effects on B16-F10 metastatic melanoma murine cells. Seven blueberry cultivars cultivated in Romania were used. The blueberry extracts were purified over an Amberlite XAD-7 resin and a Sephadex LH-20 column, in order to obtain the anthocyanin rich fractions (ARF). The antioxidant activity of the ARF of all cultivars was evaluated by ABTS, CUPRAC and ORAC assays. High performance liquid chromatography followed by electrospray ionization mass spectrometry (HPLC-ESI-MS) was used to identify and quantify individual anthocyanins. The anthocyanin content of tested cultivars ranged from 101.88 to 195.01 mg malvidin-3-glucoside/100g fresh weight. The anthocyanin rich-fraction obtained from cultivar Torro (ARF-T) was shown to have the highest anthocyanin content and antioxidant activity, and inhibited B16-F10 melanoma murine cells proliferation at concentrations higher than 500 μg/ml. In addition, ARF-T stimulated apoptosis and increased total LDH activity in metastatic B16-F10 melanoma murine cells. These results indicate that the anthocyanins from blueberry cultivar could be used as a chemopreventive or adjuvant treatment for metastasis control. Copyright © 2013 Elsevier Ltd. All rights reserved.
Cao, Hongbo; Wang, Jiangbo; Dong, Xintian; Han, Yan; Ma, Qiaoli; Ding, Yuduan; Zhao, Fei; Zhang, Jiancheng; Chen, Haijiang; Xu, Qiang; Xu, Juan; Deng, Xiuxin
Carotenoids are indispensable plant secondary metabolites that are involved in photosynthesis, antioxidation, and phytohormone biosynthesis. Carotenoids are likely involved in other biological functions that have yet to be discovered. In this study, we integrated genomic, biochemical, and cellular studies to gain deep insight into carotenoid-related biological processes in citrus calli overexpressing CrtB (phytoene synthase from Pantoea agglomerans). Fortunella hindsii Swingle (a citrus relative) and Malus hupehensis (a wild apple) calli were also utilized as supporting systems to investigate the effect of altered carotenoid accumulation on carotenoid-related biological processes. Transcriptomic analysis provided deep insight into the carotenoid-related biological processes of redox status, starch metabolism, and flavonoid/anthocyanin accumulation. By applying biochemical and cytological analyses, we determined that the altered redox status was associated with variations in O2 (-) and H2O2 levels. We also ascertained a decline in starch accumulation in carotenoid-rich calli. Furthermore, via an extensive cellular investigation of the newly constructed CrtB overexpressing Fortunella hindsii Swingle, we demonstrated that starch level reducation occurred in parallel with significant carotenoid accumulation. Moreover, studying anthocyanin-rich Malus hupehensis calli showed a negative effect of carotenoids on anthocyanin accumulation. In citrus, altered carotenoid accumulation resulted in dramatic effects on metabolic processes involved in redox modification, starch degradation, and flavonoid/anthocyanin biosynthesis. These findings provided new perspectives to understand the biological importance of carotenogenesis and of the developmental processes associated with the nutritional and sensory qualities of agricultural products that accumulate carotenoids.
López de Las Hazas, María-Carmen; Mosele, Juana I; Macià, Alba; Ludwig, Iziar A; Motilva, María-José
Beneficial properties attributed to the intake of fruit and red wine have been associated with the presence of significant amounts of anthocyanins. However, their low absorption and consequent accumulation in the gut have generated the suspicion that colonic metabolites of anthocyanins are probably involved in these protective effects. Grape pomace and strawberry extracts, rich in malvidin- and pelargonidin-glucoside, respectively, were fermented in vitro using human feces as microbial inoculum. After 8 h of anaerobic incubation, the anthocyanins were almost completely degraded, whereas their microbial metabolite concentrations were highest at 24 h. Syringic acid and tyrosol were the main metabolites of grape and strawberry extracts, respectively. On the basis of the metabolites detected, metabolic pathways of malvidin- and pelargonidin-glucosides were proposed. Anthocyanin-rich grape and strawberry extracts and their generated metabolites such as hydroxyphenylacetic acid showed apoptotic effects in HT-29 colon cancer cells and may suggest their possible contribution as anticarcinogenic agents.
Das, Prasanta Kumar; Geul, Bang; Choi, Sang-Bong; Yoo, Sang-Dong
Light is the ultimate energy source for photo-autotrophs on earth. For green plants, however, it can also be toxic under certain stressful environmental conditions and at critical developmental stages. Anthocyanins, a class of flavonoids, act as an effective screening mechanism that allows plant survival and proliferation under occasional periods of harmful irradiation through modulation of light absorption. Apart from light-sensing through photoreceptors such as phytochrome and cryptochrome, plants use the photosynthetic electron transfer (PET) chain to integrate light information. The redox status of the plastoquinone (PQ) pool of the PET chain regulates anthocyanin biosynthesis genes, together with the plant hormone ethylene and plant hormone-like sugars. A complex signaling apparatus in acyanic cells appears to transduce information to cyanic cells to regulate anthocyanin production through an intercellular signaling pathway that remains largely uncharacterized. This review will highlight recent advances in this field and their implications for the regulation of anthocyanin pigmentation. PMID:21248473
Welch, Cara R.; Wu, Qingli; Simon, James E.
Anthocyanins are a class of polyphenols responsible for the orange, red, purple and blue colors of many fruits, vegetables, grains, flowers and other plants. Consumption of anthocyanins has been linked as protective agents against many chronic diseases and possesses strong antioxidant properties leading to a variety of health benefits. In this review, we examine the advances in the chemical profiling of natural anthocyanins in plant and biological matrices using various chromatographic separations (HPLC and CE) coupled with different detection systems (UV, MS and NMR). An overview of anthocyanin chemistry, prevalence in plants, biosynthesis and metabolism, bioactivities and health properties, sample preparation and phytochemical investigations are discussed while the major focus examines the comparative advantages and disadvantages of each analytical technique. PMID:19946465
Das, Prasanta Kumar; Geul, Bang; Choi, Sang-Bong; Yoo, Sang-Dong; Park, Youn-Il
Light is the ultimate energy source for photo-autotrophs on earth. For green plants, however, it can also be toxic under certain stressful environmental conditions and at critical developmental stages. Anthocyanins, a class of flavonoids, act as an effective screening mechanism that allows plant survival and proliferation under occasional periods of harmful irradiation through modulation of light absorption. Apart from light-sensing through photoreceptors such as phytochrome and cryptochrome, plants use the photosynthetic electron transfer (PET) chain to integrate light information. The redox status of the plastoquinone (PQ) pool of the PET chain regulates anthocyanin biosynthesis genes, together with the plant hormone ethylene and plant hormone-like sugars. A complex signaling apparatus in acyanic cells appears to transduce information to cyanic cells to regulate anthocyanin production through an intercellular signaling pathway that remains largely uncharacterized. This review will highlight recent advances in this field and their implications for the regulation of anthocyanin pigmentation.
Our research group has worked the last seven years on developing black raspberries with improved disease resistance and phytochemical traits. We have been awarded USDA/NIFA-Specialty Crops Research Initiative (SCRI) funding to continue our project as a multi-region and international collaboration en...
Our research group has worked the last seven years on improving the phenological, vegetative, and phytochemical traits of U.S. grown black raspberries. We have been awarded USDA/NIFA-Specialty Crops Research Initiative (SCRI) funding to continue our project as a multi-region and international collab...
Our research group has worked the last 7 years on improving the phenological, vegetative, and phytochemical traits of US grown black raspberries. We have been awarded USDA/NIFA-Specialty Crops Research Initiative (SCRI) funding to continue our project as a multi-region and international collaboratio...
Kitdamrongsont, Kasipong; Pothavorn, Pongsagon; Swangpol, Sasivimon; Wongniam, Siripope; Atawongsa, Kanokporn; Svasti, Jisnuson; Somana, Jamorn
Anthocyanins were isolated from male bracts of 10 wild species of bananas (Musa spp. and Ensete spp.) distributed in Thailand. Six major anthocyanin pigments were identified by high performance liquid chromatography (HPLC), mass spectrometry (MS), and tandem mass spectrometry (MS/MS). They are delphinidin-3-rutinoside (m/z 611.2), cyanidin-3-rutinoside (m/z 595.8), petunidin-3-rutinoside (m/z 624.9), pelargonidin-3-rutinoside (m/z 579.4), peonidin-3-rutinoside (m/z 608.7), and malvidin-3-rutinoside (m/z 638.8). On the basis of the types of pigment present, the wild bananas can be divided into 5 groups. The first group comprises M. itinerans, Musa sp. one, Musa sp. two, and M. acuminata accessions, which contain almost or all anthocyanin pigments except for pelargonidin-3-rutinoside, including both nonmethylated and methylated anthocyanins. The second group, M. acuminata subsp. truncata, contains only malvidin-3-rutinoside while the third group, M. coccinea, contains cyanidin-3-rutinoside and pelargonidin-3-rutinoside. The forth group, M. acuminata yellow bract and E. glaucum do not appear to contain any anthocyanin pigment. The fifth group consists of M. balbisiana, M. velutina, M. laterita, and E. superbum which contain only nonmethylated anthocyanin, delphinidin-3-rutinoside, and cyanidin-3-rutinoside. Total anthocyanin content in the analyzed bracts ranged from 0-119.70 mg/100 g bract fresh weight. The differences in the type of anthocyanin and variation in the amounts present indicate that wild bananas show biochemical diversity, which may be useful for identifying specific groups of bananas or for clarifying the evolution of flavonoid metabolism in each banana group.
Wang, Lu; Dai, Silan; Jin, Xuehua; Huang, He; Hong, Yan
Anthocyanin biosynthesis is one of the thoroughly studied enzymatic pathways in biology, but little is known about the molecular mechanisms of its final stage: the transport of the anthocyanins into the vacuole. A clear picture of the dynamic trafficking of flavonoids is only now beginning to emerge. So far four different models have been proposed to explain the transport of anthocyanins from biosynthetic sites to the central vacuole, and four types of transporters have been found associated with the transport of anthocyanins: glutathione S-transferase, multidrug resistance-associated protein, multidrug and toxic compound extrusion, bilitranslocase-homologue. The functions of these proteins and related genes have also been studied. Although different models have been proposed, cellular and subcellular information is still lacking for reconciliation of different lines of evidence in various anthocyanin sequestration studies. According to the information available, through sequence analysis, gene expression analysis, subcellular positioning and complementation experiments, the function and location of these transporters can be explored, and the anthocyanin transport mechanism can be better understood.
Bautista-Ortín, Ana Belén; Martínez-Hernández, Alejandro; Ruiz-García, Yolanda; Gil-Muñoz, Rocío; Gómez-Plaza, Encarna
The rate of tannin extraction was studied in a vinification of red grapes and the results compared with another vinification made with white grapes fermented as for typical red wine, in the presence of skins and seeds. Even though the grapes presented a quite similar skin and seed tannin content, the differences in tannin concentration between both vinifications was very large, despite the fact that the only apparent difference between the phenolic composition of both wines was the anthocyanin content. This suggests that anthocyanins play an important role in tannin extractability, perhaps because they affect the extent of the tannin-cell wall interaction, a factor that largely controls the resulting quantity of tannins in wines. To confirm this observation, the effect of anthocyanins on the tannin extractability from grape seeds and skin and on the interaction between tannins and grape cell walls suspended in model solutions were studied. The results indicated that anthocyanins favored skin and seed tannin extraction and that there is a competition for the adsorption sites between anthocyanins and tannins that increases the tannin content when anthocyanins are present.
A study of the mass spectroscopic behaviors of anthocyanins in the negative ionization mode was reported and it can be used for differentiation anthocyanins from other non-anthocyanin polyphenols. For the study, an ultra-high performance liquid chromatography with high resolution mass spectrometry (...
Jiang, Mingmin; Ren, Li; Lian, Hongli; Liu, Yang; Chen, Huoying
Eggplant is rich in anthocyanins, which are the major secondary metabolites and beneficial to human health. We discovered that the anthocyanin biosynthesis of eggplant cultivar 'Lanshan Hexian' was regulated by light. In this study, we isolated two blue light receptor genes, SmCRY1 and SmCRY2, and negative/positive anthocyanin regulatory factors SmCOP1 and SmHY5 from eggplant. In terms of transcript levels, SmCRY1, SmCRY2 and SmHY5 were up-regulated by light, while SmCOP1 was down-regulated. Subsequently, the four genes were functionally complemented in phenotype of corresponding mutants, indicating that they act as counterparts of Arabidopsis genes. Yeast two-hybrid and bimolecular fluorescence complementation assays showed that SmCRY1 and SmCRY2 interact with SmCOP1 in a blue-light-dependent manner. It also obtained the result that SmCOP1 interacts with SmHY5 and SmMYB1. Furthermore, using yeast one-hybrid assay, we found that SmHY5 and SmMYB1 both bind the promoters of anthocyanin biosynthesis structural genes (SmCHS and SmDFR). Taken together, blue-light-triggered CRY1/CRY2-COP1 interaction creates the condition that HY5 and MYB1 combine with the downstream anthocyanin synthesis genes (CHS and DFR) in eggplant. Our finding provides a new working model by which light controls anthocyanin accumulation in eggplant. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.
Zhang, Yanjie; Hu, Zongli; Chu, Guihua; Huang, Cheng; Tian, Shibing; Zhao, Zhiping; Chen, Guoping
Eggplant (Solanum melongena L.) is an edible fruit vegetable cultivated and consumed worldwide. The purple eggplant is more eye-catching and popular for the health-promoting anthocyanins contained in the fruit skin. Two kinds of anthocyanin were separated and identified from purple cultivar (Zi Chang) by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. To investigate the molecular mechanisms of anthocyanin accumulation in eggplant, the transcripts of anthocyanin biosynthetic and regulatory genes were analyzed in the fruit skin and the flesh of the purple cultivar and the white cultivar (Bai Xue). Compared with the other tissues, SmMYB1 and all anthocyanin biosynthetic genes except PAL were dramatically upregulated in the fruit skin of the purple cultivar. Overexpression of SmMYB1 activated abundant anthocyanin accumulation in the regenerating shoots of eggplant. These results prove that transcriptional activation of SmMYB1 accounts for constitutive upregulation of most anthocyanin biosynthetic genes and the onset of anthocyanin biosynthesis in the purple cultivar.
Nakagawa, Kiyotaka; Maruyama, Yumiko; Miyazawa, Teruo
The data accumulated from epidemiological studies suggests that individuals with elevated blood levels of homocysteine have an increased risk of cardiovascular disease. However, little is known of the food factor that may affect the homocysteine status, except for folate and B-vitamins. Here, we tested the effect of dietary phenolics (i.e., anthocyanin of food colorant) administration on plasma homocysteine concentration in a rat study, since a profound effect on the methionine metabolism was speculated from the 3',4'-catechol skeletal structure of anthocyanin. Female Sprague-Dawley rats (body weight 100 g) orally ingested a single dose of anthocyanin mixture (total 100 mg) composed of cyanidin-3-glucoside (50mg), cyanidin-3-sambubioside (48 mg), and cyanidin-3,5-diglucoside (2 mg). The total homocysteine in the plasma collected 90-240 min after anthocyanin intake was 1.4 to 1.8-fold (5.2-6.7 micromol/L) higher than the basal homocysteine level (3.7 micromol/L). In the liver and kidney, anthocyanin significantly affects sulfur amino acid (S-adenosylmethionine, SAM, and S-adenosylhomocysteine, SAH) levels, both of which are precursors of plasma homocysteine, and the SAH/SAM ratio showed a significant increase in the liver and kidney. Accordingly, these results suggest that dietary anthocyanin stimulates homocysteine synthesis from SAH in the liver and kidney, and the homocysteine yielded transfers into the blood stream. The intake of anthocyanin and its structural homologues may have an effect on the metabolic regulation of sulfur amino acids and possibly increase the risk of vascular disease in humans.
Bae, Ji-Young; Lim, Soon Sung; Kim, Sun Ju; Choi, Jung-Suk; Park, Jinseu; Ju, Sung Mi; Han, Seoung Jun; Kang, Il-Jun; Kang, Young-Hee
Fruits of bog blueberry (Vaccinium uliginosum L.) are rich in anthocyanins that contribute pigmentation. Anthocyanins have received much attention as agents with potentials preventing chronic diseases. This study investigated the capacity of anthocyanin-rich extract from bog blueberry (ATH-BBe) to inhibit photoaging in UV-B-irradiated human dermal fibroblasts. BBe anthocyanins were detected as cyanidin-3-glucoside, petunidin-3-glucoside, malvidin-3-glucoside, and delphinidin3-glucoside. ATH-BBe attenuated UV-B-induced toxicity accompanying reactive oxygen species (ROS) production and the resultant DNA damage responsible for activation of p53 and Bad. Preincubation of ATH-BBe markedly suppressed collagen degradation via blunting production of collagenolytic matrix metalloproteinases (MMP). Additionally, ATH-BBe enhanced UV-B-downregulated procollagen expression at transcriptional levels. We next attempted to explore whether ATH-BBe mitigated the MMP-promoted collagen degradation through blocking nuclear factor kappaB (NF-kappaB) activation and MAPK-signaling cascades. UV-B radiation enhanced nuclear translocation of NF-kappaB, which was reversed by treatment with ATH-BBe. The UV-B irradiation rapidly activated apoptosis signal-regulating kinase-1 (ASK-1)-signaling cascades of JNK and p38 mitogen-activated protein kinase (p38 MAPK), whereas ATH-BBe hampered phosphorylation of c-Jun, p53, and signal transducers and activators of transcription-1 (STAT-1) linked to these MAPK signaling pathways. ATH-BBe diminished UV-B augmented-release of inflammatory interleukin (IL)-6 and IL-8. These results demonstrate that ATH-BBe dampens UV-B-triggered collagen destruction and inflammatory responses through modulating NF-kappaB-responsive and MAPK-dependent pathways. Therefore, anthocyanins from edible bog blueberry may be protective against UV-induced skin photoaging.
Stebbins, Nathan B; Howard, Luke R; Prior, Ronald L; Brownmiller, Cindi; Mauromoustakos, Andy
Blackberry anthocyanins provide attractive color and antioxidant activity. However, anthocyanins degrade during juice processing and storage, so maintaining high anthocyanin concentrations in berry juices may lead to greater antioxidant and health benefits for the consumer. This study evaluated potential additives to stabilize anthocyanins during blackberry juice storage. The anthocyanin stabilizing agents used were: glutathione, galacturonic acid, diethylenetriaminepentaacetic acid and tannic acid, which were added at a level of 500 mg L(-1). Juice anthocyanin, flavonol, and ellagitannin content and percent polymeric color were measured over five weeks of accelerated storage at 30 °C. Glutathione had the greatest protective effect on total anthocyanins and polymeric color. Therefore a second study was performed with glutathione in combination with lipoic and ascorbic acids in an effort to use antioxidant recycling to achieve a synergistic effect. However, the antioxidant recycling system had no protective effect relative to glutathione alone. Glutathione appears to be a promising blackberry juice additive to protect against anthocyanin degradation during storage.
Rahim, Md Abdur; Busatto, Nicola; Trainotti, Livio
MYB10.1 and MYB10.3, with bHLH3, are the likely regulators of anthocyanin biosynthesis in peach fruit. MYB10.1/2/3 forms a cluster on the same genomic fragment where the Anther color ( Ag ) trait is located. Anthocyanins are bioactive compounds responsible for the pigmentation of many plant parts such as leaves, flowers, fruits and roots, and have potential benefits to human health. In peach [Prunus persica (L.) Batsch], peel color is a key determinant for fruit quality and is regulated by flavonoids including anthocyanins. The R2R3 MYB transcription factors (TFs) control the expression of anthocyanin biosynthetic genes with the help of co-activators belonging to the basic-helix-loop-helix (bHLH) and WD40 repeat families. In the peach genome six MYB10-like and three bHLH-like TFs were identified as candidates to be the regulators of the anthocyanin accumulation, which, in yellow flesh fruits, is highest in the peel, abundant in the part of the mesocarp surrounding the stone and lowest in the mesocarp. The expression of MYB10.1 and MYB10.3 correlates with anthocyanin levels of different peach parts. They also have positive correlation with the expression of key structural genes of the anthocyanin pathway, such as CHS, F3H, and UFGT. Functions of peach MYB10s were tested in tobacco and shown to activate key genes in the anthocyanin pathway when bHLHs were co-expressed as partners. Overexpression of MYB10.1/bHLH3 and MYB10.3/bHLH3 activated anthocyanin production by up-regulating NtCHS, NtDFR and NtUFGT while other combinations were not, or much less, effective. As three MYB10 genes are localized in a genomic region where the Ag trait, responsible for anther pigmentation, is localized, it is proposed they are key determinant to introduce new peach cultivars with higher antioxidant level and pigmented fruit.
Liu, Yixiang; Song, Xue; Han, Yong; Zhou, Feng; Zhang, Di; Ji, Baoping; Hu, Jimei; Lv, Yechun; Cai, Shengbao; Wei, Ying; Gao, Fengyi; Jia, Xiaonan
Studies suggest that the consumption of berry fruits rich in anthocyanins may have beneficial effects on improving visual function. This study determined the total polyphenol and total anthocyanin contents in wild Chinese blueberries using the Folin-Ciocalteu reagent method and a pH differential method. Anthocyanin composition and quantity were characterized by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry coupled with mass selective detection. Total polyphenol and anthocyanin contents were 602.9 ± 9.2 and 177.8 ± 8.3 mg/100 g, respectively. Seventeen anthocyanins were discovered, and only 13 were tentatively identified in the wild blueberries. Anthocyanins of malvidin glycosylated with hexose or pentose accounted for >46% of total anthocyanin content. Furthermore, the effect of whole blueberries on retinal damage in pigmented rabbits upon light exposure was investigated, and the retinal functions were evaluated by electroretinogram (ERG). Pigmented rabbits were chosen for this experiment because of their large eyes, which facilitated the operative procedure and observation, and the similarity of their eyes to the human eye structure. Light-induced retinal damage was induced by exposure to white light at 15000 ± 1000 lx for 2 h. Feeding the rabbits with blueberries at a dosage of 1.2 or 4.9 g/kg/day for 4 weeks prior to light exposure effectively reduced photodamage to the retinas. This study adds to the growing body of data supporting the bioactivity of blueberries in improving mammal vision.
Bernal, Freddy A; Orduz-Diaz, Luisa L; Coy-Barrera, Ericsson
Anthocyanins are natural pigments known for their color and antioxidant activity. These properties allow their use in various fields, including food and pharmaceutical ones. Quantitative determination of anthocyanins had been performed by non-specific methods that limit the accuracy and reliability of the results. Therefore, a novel, simple spectrophotometric method for the anthocyanins quantification based on a formation of blue-colored complexes by the known reaction between catechol- and pyrogallol-containing anthocyanins and aluminum(III) is presented. The method demonstrated to be reproducible, repetitive (RSD<1.5%) and highly sensitive to ortho-dihydroxylated anthocyanins (LOD = 0.186 μg/mL). Compliance with Beer's law was also evident in a range of concentrations (2-16 μg/mL for cyanidin 3-O-glucoside). Good recoveries (98.8-103.3%) were calculated using anthocyanin-rich plant samples. The described method revealed direct correlation to pH differential method results for several common anthocyanin-containing fruits indicating its great analytical potential. The presented method was successfully validated.
Passamonti, Sabina; Vrhovsek, Urska; Mattivi, Fulvio
Bilitranslocase (TC 2.A.65.1.1) is an organic anion membrane carrier expressed at the sinusoidal domain of the liver plasma membrane and in epithelial cells of the gastric mucosa. Its substrates are sulfobromophthalein, bilirubin, and nicotinic acid. This work reports on the identification of a new class of bilitranslocase substrates, i.e., anthocyanins. Seventeen out thes 20 compounds tested behaved as competitive inhibitors of bilitranslocase transport activity (K(I)=1.4-22 microM). Their structure-activity relationship reveals that mono- and di-glucosyl anthocyanins, the anthocyanin species occurring in food, are better ligands than the corresponding aglycones. Moreover, the first interaction of anthocyanins with the carrier occurs through hydrophilic moieties, such as the 3-glucosyl moiety and the B ring for the monoglucosides, through the 5-glucosyl moiety and the A ring for the diglucosides, and through either the B or the A ring for the aglycones. These findings suggest that bilitranslocase could play a role in the bioavailability of anthocyanins.
Osmani, Sarah Anne; Hansen, Esben Halkjaer; Malien-Aubert, Céline; Olsen, Carl-Erik; Bak, Søren; Møller, Birger Lindberg
The effect of glucuronosylation on the color stability of anthocyanins was investigated using glucuronosylated anthocyanins isolated from the flower petals of the red daisy (Bellis perennis) or obtained by enzymatic in vitro synthesis using heterologously expressed red daisy glucuronosyltransferase BpUGT94B1. Color stability toward light and heat stress was assessed by monitoring CIELAB color coordinates and stability at pH 7.0 by A(550). Cyanidin-3-O-2''-O-glucuronosylglucoside showed improved color stability in response to light compared to both cyanidin 3-O-glucoside and cyanidin 3-O-2''-O-diglucoside. A similar increase in color stability was not observed following heat treatment. Glucuronosylation did not increase the stability of anthocyanins at pH 7.0 as determined by A(550). To test for a possible effect of glucuronosylation on the color stability of anthocyanins in plant extracts used for food coloration, an elderberry (Sambucus nigra) extract was glucuronosylated in vitro. Glucuronosylation of approximately 50% of total anthocyanins proceeded fast and resulted in increased color stability in response to both heat and light. The data show that glucuronosylation may be used to stabilize industrially used extracts of natural colorants.
This study contrasted the anthocyanins of investigational grape clusters that developed without light incidence (light-excluded), to those of control clusters that were shaded naturally beneath the vine canopy (control-shaded). Treatment grape clusters were light-excluded during ripening by opaque white polypropylene enclosures; temperature, vapor pressure deficit, and light intensity were measured continually. All 15 'Merlot' grape anthocyanins accrued in both groups, indicating no accumulations were terminated from light-exclusion during ripening. Light-excluded clusters had an overall lower anthocyanin concentration (98.1 mg/100 g of berries) than that of control clusters (162.0 mg/100 g of berries), but it was not significantly different. Light-excluded clusters showed altered concentrations of nine individual anthocyanins that were significantly higher in control-shaded clusters. Although the changes in anthocyanin composition could not be attributed solely to the elimination of light, as there were also deviations in berry temperature and vapor pressure deficit concurrent with preventing light from reaching the treatment clusters.
Esposito, Debora; Chen, Amelia; Grace, Mary H; Komarnytsky, Slavko; Lila, Mary Ann
Wild lowbush blueberries (Vaccinium angustifolium Ait) are a rich source of anthocyanins and other flavonoids with anti-inflammatory activities; however, their individual effects on cellular signaling remain to be elucidated. This study determined the capacity of blueberry bioactives to protect murine RAW 264.7 macrophages from lipopolysaccharide-induced inflammation. Fractionation of the crude extract (CE) into polyphenol-rich (PPR), anthocyanin-rich (ANC), and proanthocyanidin-rich (PAC) fractions and an ethyl acetate fraction (EA) revealed that PPR, ANC, and PAC components most effectively suppressed mRNA biomarkers of acute inflammation (Cox-2, iNOS, and IL-1β). Among major polyphenols found in the wild blueberries, malvidin-3-glucoside was significantly more effective than epicatechin or chlorogenic acid in reducing the expression of pro-inflammatory genes in vitro.
Akhavan Mahdavi, Sahar; Jafari, Seid Mahdi; Assadpoor, Elham; Dehnad, Danial
The barberry (Berberis vulgaris) extract which is a rich source of anthocyanins was used for spray drying encapsulation with three different wall materials, i.e., combination of maltodextrin and gum Arabic (MD+GA), maltodextrin and gelatin (MD+GE), and maltodextrin (MD). Response Surface Methodology (RSM) was applied for optimization of microencapsulation efficiency and physical properties of encapsulated powders considering wall material type as well as different ratios of core to wall materials as independent variables. Physical characteristics of spray-dried powders were investigated by further analyses of moisture content, hygroscopicity, degree of caking, solubility, bulk and absolute density, porosity, flowability and microstructural evaluation of encapsulated powders. Our results indicated that samples produced with MD+GA as wall materials represented the highest process efficiency and best powder quality; the optimum conditions of microencapsulation process for barberry anthocyanins were found to be the wall material content and anthocyanin load of 24.54% and 13.82%, respectively. Under such conditions, the microencapsulation efficiency (ME) of anthocyanins could be as high as 92.83%. Copyright © 2016 Elsevier B.V. All rights reserved.
He, Fei; Liang, Na-Na; Mu, Lin; Pan, Qiu-Hong; Wang, Jun; Reeves, Malcolm J; Duan, Chang-Qing
Originating in the grapes, anthocyanins and their derivatives are the crucial pigments responsible for the red wine color. During wine maturation and aging, the concentration of monomeric anthocyanins declines constantly, while numerous more complex and stable anthocyanin derived pigments are formed, mainly including pyranoanthocyanins, polymeric anthocyanins produced from condensation between anthocyanin and/or flavan-3-ols directly or mediated by aldehydes. Correspondingly, their structural modifications result in a characteristic variation of color, from purple-red color in young red wines to brick-red hue of the aged. Because of the extreme complexity of chemical compounds involved, many investigations have been made using model solutions of know composition rather than wine. Thus, there is a large amount of research still required to obtain an overall perspective of the anthocyanin composition and its change with time in red wines. Future findings may well greatly revise our current interpretation of the color in red wines. This paper summarizes the most recent advances in the studies of the anthocyanins derived pigments in red wines, as well as their color evolution.
The color of red cabbage (Brassica oleracea var. capitata) is due to anthocyanin accumulation. To investigate the regulatory control of anthocyanin production in red cabbage, the expression of anthocyanin biosynthetic and regulatory genes from eight commercial cultivars was examined. While the four ...
Nie, Qixing; Feng, Lei; Hu, Jielun; Wang, Sunan; Chen, Haihong; Huang, Xiaojun; Nie, Shaoping; Xiong, Tao; Xie, Mingyong
Blueberry products have various health benefits due to their high content of dietary anthocyanins. The aim of this study was to investigate the impact of fermentation and sterilization on total anthocyanin content, composition and some quality attributes of blueberry puree. The blueberry puree used here was fermented for 40 h at 37 °C by Lactobacillus after sterilization. The method of ultra-performance liquid chromatography-mass spectrometry was optimized for the rapid analysis of anthocyanins. Quality attributes including pH, color, total soluble solids and viscosity were measured. A total of 21 anthocyanins and five anthocyanidins were quantified by ultra-performance liquid chromatography. Fermented blueberry had reduced total anthocyanin content (29%) and levels of individual anthocyanins compared with fresh blueberry. Total anthocyanin content was decreased 46% by sterilization, and different degradation behavior of individual anthocyanin was appeared between fermented and sterilized-fermented blueberry puree. Fermentation and sterilization decreased the total soluble solids and pH and changed color parameters, while minimally influencing viscosity. The loss of total anthocyanin content by fermentation was related to the unstable structure of blueberry anthocyanins. Anthocyanins are sensitive to temperature (>80 °C), and degradation of anthocyanins by sterilization in blueberry should be considered in the fermentation procedure. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.
Su, Xiaoyu; Xu, Jianteng; Rhodes, Davina; Shen, Yanting; Song, Weixing; Katz, Benjamin; Tomich, John; Wang, Weiqun
Anthocyanins are natural pigments derived from the phenylpropanoid pathway. Most tomatoes produce little anthocyanins, but the transgenic purple tomato biosynthesizes a high level of anthocyanins due to expression of two transcription factors (Del and Ros1). This study was to identify and quantify anthocyanins in this transgenic tomato line. Seven anthocyanins, including two new anthocyanins [malvidin-3-(p-coumaroyl)-rutinoside-5-glucoside and malvidin-3-(feruloyl)-rutinoside-5-glucoside], were identified by LC-MS/MS. Petunidin-3-(trans-coumaroyl)-rutinoside-5-glucoside and delphinidin-3-(trans-coumaroyl)-rutinoside-5-glucoside were the most abundant anthocyanins, making up 86% of the total anthocyanins. Compared to undetectable anthocyanins in the wild type, the contents of anthocyanins in the whole fruit, peel, and flesh of the Del/Ros1-transgenic tomato were 5.2±0.5, 5.1±0.5, and 5.8±0.3g/kg dry matter, respectively. Anthocyanins were undetectable in the seeds of both wide-type and transgenic tomato lines. Such novel and high levels of anthocyanins obtained in this transgenic tomato may provide unique functional products with potential health benefits.
Anthocyanin gene expression has been extensively studied in leaves, fruits and flowers of numerous plants. Little, however, is known about anthocyanin accumulation in roots, or in carrots or other Apiaceae. We quantified expression of six anthocyanin biosynthetic genes (phenylalanine ammonia-lyase (...
Bononi, Monica; Tateo, Fernando
Anthocyanins can be considered spy-substances, useful in obtaining information regarding the shelf-life of food supplements containing cranberry juice or cranberry-derived extracts. The level of total anthocyanins, as evaluated by high-performance liquid chromatography-diode-array detector and analytically expressed as cyanidin aglycone, represents a 'quality index' useful for routine estimation of shelf-life. The objective of this work was to study the stability of anthocyanins in a commercial cranberry (Vaccinium macrocarpon) dried extract compared with the stability of the same extract contained in a food supplement enriched with alpha-tocopheryl succinate and ascorbic acid. The values obtained after exposure of the samples to natural light and to alternating hot and cold temperatures show considerable sensitivity of the commercial cranberry dried extract to the agents used for the same evaluation (time, temperature and light) and emphasize a positive effect of the enrichment of the derived preparation with alpha-tocopheryl succinate and ascorbic acid.
Ogata, Jun; Kanno, Yoshiaki; Itoh, Yoshio; Tsugawa, Hidehito; Suzuki, Masahiko
Anthocyanin is the principal pigment in flowers, conferring intense red-to-blue cyanic colours on petals and helping to attract pollinators. Its biosynthesis involves glycosylation steps that are important for the stability of the pigment and for its aqueous solubility in vacuoles. Here we describe anthocyanin biosynthesis in roses (Rosa hybrida), which is unlike the pathway used in other flowers in that it relies on a single enzyme to achieve glycosylation at two different positions on the precursor molecule. Phylogenetic analysis also indicates that this previously unknown glucosyltransferase enzyme may be unique to roses, with glycosylation having apparently evolved into a single stabilizing step in other plants.
Li, Xinying; Ma, Hongyan; Huang, Huilian; Li, Defu; Yao, Shun
Anthocyanins are a class of naturally occurring polyphenols which have been most widely studied in recent decades for the rapid development of relative techniques. This article first reviews the various anthocyanin resources including fruits, flowers, vegetables and beverages. Besides the direct extraction from natural resources, anthocyanins can also be obtained by semi- or total synthesis. After the introduction of new representative anthocyanins found in the past few years and the major relationships between structures and stability, modern separation and analysis technologies in related studies were summarised, which play an important role in chemical researches of anthocyanins.
Koshioka, Masaji; Umegaki, Naoko; Boontiang, Kriangsuk; Pornchuti, Witayaporn; Thammasiri, Kanchit; Yamaguchi, Satoshi; Tatsuzawa, Fumi; Nakayama, Masayoshi; Tateishi, Akira; Kubota, Satoshi
Five anthocyanins, delphinidin 3-O-rutinoside, cyanidin 3-O-rutinoside, petunidin 3-O-rutinoside, malvidin 3-O-glucoside and malvidin 3-O-rutinoside, were identified. Three anthocyanins, delphinidin 3-O-glucoside, cyanidin 3-O-glucoside and pelargonidin 3-O-rutinoside, were putatively identified based on C18 HPLC retention time, absorption spectrum, including λmax, and comparisons with those of corresponding standard anthocyanins, as the compounds responsible for the pink to purple-red pigmentation of the bracts of Curcuma alismatifolia and five related species. Cluster analysis based on four major anthocyanins formed two clusters. One consisted of only one species, C. alismatifolia, and the other consisted of five. Each cluster further formed sub-clusters depending on either species or habitats.
He, Fei; Liang, Na-Na; Mu, Lin; Pan, Qiu-Hong; Wang, Jun; Reeves, Malcolm J; Duan, Chang-Qing
Originating in the grapes, monomeric anthocyanins in young red wines contribute the majority of color and the supposed beneficial health effects related to their consumption, and as such they are recognized as one of the most important groups of phenolic metabolites in red wines. In recent years, our increasing knowledge of the chemical complexity of the monomeric anthocyanins, their stability, together with the phenomena such as self-association and copigmentation that can stabilize and enhance their color has helped to explain their color representation in red wine making and aging. A series of new enological practices were developed to improve the anthocyanin extraction, as well as their color expression and maintenance. This paper summarizes the most recent advances in the studies of the monomeric anthocyanins in red wines, emphasizing their origin, occurrence, color enhancing effects, their degradation and the effect of various enological practices on them.
Celli, Giovana Bonat; Ghanem, Amyl; Brooks, Marianne Su-Ling
Haskap berries (Lonicera caerulea L.) are a rich source of bioactive molecules. As such, the extraction of anthocyanins is important for the development of many value-added products and functional food ingredients. In this paper, the ultrasound-assisted extraction (UAE) of anthocyanins from haskap berries was investigated. Significant independent variables were screened and optimized using Plackett-Burman (PB) and Box-Behnken (BB) designs, respectively. The mathematical model showed a high coefficient of determination (R(2)=0.9396) and the optimum conditions for the extraction were as follows: liquid/solid ratio 25:1 (mL/g), solvent composition of 80% ethanol, addition of 0.5% formic acid, ultrasound bath temperature of 35°C for 20 min. Under these conditions, the total anthocyanin content of 22.73 mg cyaniding 3-glucoside equivalents (C3G)/g dry weight (DW) was consistent with the predicted response of 22.45 mg C3G/g DW from the model (mean error of 1.28%). Five anthocyanins were identified in the optimized extract, namely cyanidin 3,5-diglucoside, cyanidin 3-glucoside, cyanidin 3-rutinoside, pelargonidin 3-glucoside, and peonidin 3-glucoside. Thus, UAE is a suitable technique for the extraction of anthocyanins from haskap berries.
Cassidy, Aedín; Bertoia, Monica; Chiuve, Stephanie; Flint, Alan; Forman, John; Rimm, Eric B
Background: Although increased fruit intake reduces cardiovascular disease (CVD) risk, which fruits are most beneficial and what key constituents are responsible are unclear. Habitual intakes of flavonoids, specifically anthocyanins and flavanones, in which >90% of habitual intake is derived from fruit, are associated with decreased CVD risk in women, but associations in men are largely unknown. Objective: We examined the relation between habitual anthocyanin and flavanone intake and coronary artery disease and stroke in the Health Professionals Follow-Up Study. Design: We followed 43,880 healthy men who had no prior diagnosed CVD or cancer. Flavonoid intake was calculated with the use of validated food-frequency questionnaires. Results: During 24 y of follow-up, 4046 myocardial infarction (MI) and 1572 stroke cases were confirmed by medical records. Although higher anthocyanin intake was not associated with total or fatal MI risk, after multivariate adjustment an inverse association with nonfatal MI was observed (HR: 0.87; 95% CI: 0.75, 1.00; P = 0.04; P-trend = 0.098); this association was stronger in normotensive participants (HR: 0.81; 95% CI: 0.69, 0.96; P-interaction = 0.03). Anthocyanin intake was not associated with stroke risk. Although flavanone intake was not associated with MI or total stroke risk, higher intake was associated with a lower risk of ischemic stroke (HR: 0.78; 95% CI: 0.62, 0.97; P = 0.03, P-trend = 0.059), with the greatest magnitude in participants aged ≥65 y (P-interaction = 0.04). Conclusions: Higher intakes of fruit-based flavonoids were associated with a lower risk of nonfatal MI and ischemic stroke in men. Mechanistic studies and clinical trials are needed to unravel the differential benefits of anthocyanin- and flavanone-rich foods on cardiovascular health. PMID:27488237
Cui, Chun; Zhang, Shaomin; You, Lijun; Ren, Jiaoyan; Luo, Wei; Chen, Wenfen; Zhao, Mouming
The anthocyanins in the fruits of Rhodomyrtus tomentosa (ACN) were extracted by 1% TFA in methanol, and then purified by X-5 resin column and C18 (SPE) cartridges. The purified anthocyanin extract (ART) from the fruits of R. tomentosa showed strong antioxidant activities, including DPPH radical-scavenging capacity, ABTS radical scavenging capacity, reducing power and oxygen radical absorbance capacity (ORAC). The purified anthocyanin extract was analyzed by high performance liquid chromatography (HPLC). The major anthocyanins were purified by semi-preparative HPLC and Sephadex LH-20 column chromatography, and were identified as cyanidin-3-O-glucoside, peonidin-3-O-glucoside, malvidin-3-O-glucoside, petunidin-3-O-glucoside, delphinidin-3-O-glucoside and pelargonidin-3-glucoside by HPLC-ESI/MS and nuclear magnetic resonance spectroscopy (NMR). Cyanidin-3-O-glucoside was considered as the most abundant anthocyanin, which was 29.4 mg/100 g dry weight of R. tomentosa fruits. Additionally, all the major anthocyanins were identified from R. tomentosa fruit for the first time.
This research was conducted to clarify anthocyanin accumulation within ‘Merlot’ grapes in response to microclimate, specifically to light incidence, temperature, and humidity. Treatment grape clusters were light-excluded during ripening by opaque white polypropylene enclosures, during which light in...
The pH differential method (AOAC method 2005.02) by spectrophotometer, and high performance liquid chromatography (HPLC) are methods commonly used by researchers and the food industry for quantifying anthocyanins of samples or products. This study was carried out to establish a relationship between...
The pH differential method (AOAC method 2005.02) by spectrophotometer and high performance liquid chromatography (HPLC) are methods commonly used by researchers and the food industry for quantifying anthocyanins of samples or products. This study was carried out to establish a relationship between t...
The pH differential method (AOAC method 2005.02) by spectrophotometer, and high performance liquid chromatography (HPLC) are methods commonly used by researchers and the food industry for quantifying anthocyanins of samples or products. This study was carried out to establish a relationship between ...
This study contrasted the anthocyanins of investigational grape clusters that developed without light incidence (light-excluded), to those of control clusters that were shaded naturally beneath the vine canopy (control-shaded). Treatment grape clusters were light-excluded during ripening by opaque w...
Willemse, Chandré M; Stander, Maria A; de Villiers, André
Hydrophilic interaction chromatography (HILIC) provides an alternative separation mode for the analysis of phenolic compounds, in which aqueous-organic mobile phases with polar stationary phases are used. This paper reports the evaluation of HILIC for the analysis of the natural pigments anthocyanins, which are of importance because of their chromophoric properties and a range of health benefits associated with their consumption. Several HILIC stationary phases (silica, diol, amine, cyanopropyl and amide) and mobile phase combinations were evaluated, with the latter proving particularly important due to the distinctive chromatographic behaviour of anthocyanins. Diode array detection was used for selective detection of anthocyanins, while high resolution quadrupole-time-of-flight mass spectrometry (Q-TOF-MS) was used for compound identification. The potential of HILIC separation is demonstrated for a range of anthocyanins varying in glycosylation and acylation patterns found in blueberries, grape skins, black beans, red cabbage and red radish. HILIC is shown to be a complementary separation method to reversed phase liquid chromatography (RP-LC) due to the alternative retention mechanism.
Jennings, Amy; Welch, Ailsa A; Spector, Tim; Macgregor, Alex; Cassidy, Aedín
Although laboratory data suggest that several flavonoid subclasses are involved in glucose metabolism, limited clinical and epidemiologic data are available. The current study examined associations between habitual intake of flavonoid subclasses, insulin resistance, and related inflammatory biomarkers. In a cross-sectional study of 1997 females aged 18-76 y, intakes of total flavonoids and their subclasses (flavanones, anthocyanins, flavan-3-ols, polymeric flavonoids, flavonols, flavones) were calculated from food frequency questionnaires using an extended USDA database. Fasting serum glucose, insulin, high-sensitivity C-reactive protein (hs-CRP; n = 1432), plasminogen activator inhibitor-1 (n = 843), and adiponectin (n = 1452) concentrations were measured. In multivariable analyses, higher anthocyanin and flavone intake were associated with significantly lower peripheral insulin resistance [homeostasis model assessment of insulin resistance; quintile 5 (Q5) to Q1 = -0.1, P-trend = 0.04 for anthocyanins and flavones] as a result of a decrease in insulin concentrations (Q5-Q1 = -0.7 μU/mL, P-trend = 0.02 anthocyanins; Q5-Q1 = -0.5 μU/mL, P-trend = 0.02 flavones). Higher anthocyanin intake was also associated with lower hs-CRP concentrations (Q5-Q1 = -0.3 mg/L, P-trend = 0.04), whereas those in the highest quintile of flavone intake had improved adiponectin concentrations (Q5-Q1 = 0.7 μg/L, P-trend = 0.01). Anthocyanin-rich foods were also associated with lower insulin and inflammation levels. No significant associations were observed for total or other flavonoid subclasses. Higher intakes of both anthocyanins and flavones were associated with improvements in insulin resistance and hs-CRP. These associations were found with intakes readily achieved in the diet. The observed reduction in insulin concentrations was similar to that reported previously for other lifestyle factors. Dose-response trials are needed to ascertain optimal intakes for the potential reduction
He, Bo; Ge, Jiao; Yue, Pengxiang; Yue, XueYang; Fu, Ruiyan; Liang, Jin; Gao, Xueling
The optimal preparation parameters to create anthocyanin-loaded chitosan nanoparticles was predicted using response surface methodology (RSM). A Box-Behnken design was used to determine the preparation parameters that would achieve the preferred particle size and high encapsulation efficiency. The result suggested that the optimized conditions were 2.86mg/mL carboxymethyl chitosan (CMC), 0.98mg/mL chitosan hydrochloride (CHC) and 5.97mg anthocyanins. Using the predicted amounts, the experimentally prepared particles averaged 219.53nm with 63.15% encapsulation efficiency. The result was less than 5% different than the predicted result of 214.83nm particle size and 61.80% encapsulation efficiency. Compared with the free anthocyanin solution, the anthocyanin-loaded chitosan nanoparticles showed a slowed degradation in simulated gastrointestinal fluid. Compared with the free anthocyanin solutions in a model beverage system, the stability of the anthocyanins was increased in the anthocyanin-loaded chitosan nanoparticles.
Nicoué, Eugéne Emile; Savard, Sylvain; Belkacemi, Khaled
Anthocyanins were extracted from a mixture of berries of Vaccinium angustifolium and Vaccinium myrtilloïdes at 7.7 degrees C, 26 degrees C, and 79 degrees C using ethanol alone or ethanol acidified with hydrochloric, citric, tartaric, lactic, or phosphoric acids at a solvent to solid ratio of 10. The effect of these parameters on extracted anthocyanins stability was investigated. The pH-differential and HPLC-DAD methods were used to determine anthocyanin contents. Extracted anthocyanins were purified on a C-18 solid-phase extraction cartridge and characterized by HPLC/electrospray ionization/mass spectrometry (HPLC-ESI-MS/MS). Anthocyanins were identified according to their HPLC retention times, elution order, and MS fragmentation pattern and by comparison with standards and published data. Anthocyanin extractions gave different yields depending on the type of added acid and the extraction temperature. High yields of monomeric and total anthocyanins (26.3 and 28.9 mg/g of dry matter) were obtained at 79 degrees C using phosphoric acid. Extraction using tartaric acid at 79 degrees C provided the lowest degradation index (1.05). Anthocyanins were stable and browning by polyphenol oxidase was inhibited under these conditions. Of the six common anthocyanindins, five were identified in the extracts, namely, delpinidin, cyanidin, peonidin, petunidin, and malvidin; pelargonidin was not found. In addition to well-known major anthocyanins, new anthocyanins were identified for the first time in extracts of wild blueberries from Quebec.
Chaiamornnugool, Phrompak; Tontapha, Sarawut; Phatchana, Ratchanee; Ratchapolthavisin, Nattawat; Kanokmedhakul, Somdej; Sang-aroon, Wichien; Amornkitbamrung, Vittaya
The low cost DSSCs utilized by crude and pre-concentrated anthocyanins extracted from six anthocyanin-rich samples including mangosteen pericarp, roselle, red cabbage, Thai berry, black rice and blue pea were fabricated. Their photo-to-current conversion efficiencies and stability were examined. Pre-concentrated extracts were obtained by solid phase extraction (SPE) using C18 cartridge. The results obviously showed that all pre-concentrated extracts performed on photovoltaic performances in DSSCs better than crude extracts except for mangosteen pericarp. The DSSC sensitized by pre-concentrated anthocyanin from roselle and red cabbage showed maximum current efficiency η = 0.71% while DSSC sensitized by crude anthocyanin from mangosteen pericarp reached maximum efficiency η = 0.97%. In addition, pre-concentrated extract based cells possess more stability than those of crude extract based cells. This indicates that pre-concentration of anthocyanin via SPE method is very effective for DSSCs based on good photovoltaic performance and stability. The DFT/TDDFT calculations of electronic and photoelectrochemical properties of the major anthocyanins found in the samples are employed to support the experimental results.
Lefevre, M; Wiles, J; Zhang, X; Howard, L; Gupta, S; Smith, A; Ju, ZY; DeLany, JP
The mechanism(s) through which fruits, vegetables and whole grains favorably affect health is not well established. Employing an anthocyanin-rich grape as a model, we examined the ability of an agnostic analytical approach employing gene expression microarrays, to generate novel testable hypotheses regarding the mechanisms of action of potentially healthful foods and food components. C57Bl/6 mice were divided into two groups and fed a proatherogenic diet with or without a semi-purified anthocyanin extract (70% anthocyanins) incorporated at a level of 0.1 mg/ml into the drinking water. After six weeks, compared to control mice, mice supplemented with anthocyanins tended to gain more weight and have increased adipose tissue mass, although these effects did not achieve statistical significance. Anthocyanin supplemented mice had significantly reduced relative liver weights and heart weights. Serum lipids and inflammatory cytokines were not different between the groups. Gene expression microarray analysis of the liver and skeletal muscle identified a number molecular pathways significantly affected by anthocyanin treatment. Two distinct clusters emerged. The first cluster included down-regulated pathways in both muscle and liver involving cellular defense while the second included hepatic genes involved in energy metabolism. From these data three hypotheses were developed for future investigation. PMID:18555855
Liu, Xiaoqiang; Xiang, Min; Fan, Yufang; Yang, Chunxian; Zeng, Lingjiang; Zhang, Qitang; Chen, Min; Liao, Zhihua
Purple-fleshed sweet potato is good for health due to rich anthocyanins in tubers. Although the anthocyanin biosynthetic pathway is well understood in up-ground organs of plants, the knowledge on anthocyanin biosynthesis in underground tubers is limited. In the present study, we isolated and functionally characterized a root-preferential gene encoding dihydrokaempferol reductase (IbDHKR) from purple-fleshed sweet potato. IbDHKR showed highly similarity with the reported dihydroflavonol reductases in other plant species at the sequence levels and the NADPH-binding motif and the substrate-binding domain were also found in IbDHKR. The tissue profile showed that IbDHKR was expressed in all the tested organs, but with much higher level in tuber roots. The expression level of IbDHKR was consistent with the anthocyanin content in sweet potato organs, suggesting that tuber roots were the main organs to synthesize anthocyanins. The recombinant 44 kD IbDHKR was purified and fed by three different dihydroflavonol substrates including dihydrokaempferol (DHK), dihydroquerctin, and dihydromyrecetin. The substrate feeding assay indicated that only DHK could be accepted as substrate by IbDHKR, which was reduced to leucopelargonidin confirmed by LC-MS. Finally, IbDHKR was overexpressed in transgenic tobacco. The IbDHKR-overexpression tobacco corolla was more highly pigmented and contained higher level of anthocyanins than the wild-type tobacco corolla. In summary, IbDHKR was a root-preferential gene involved in anthocyanin biosynthesis and its encoding protein, specifically catalyzing DHK reduction to yield leucopelargonidin, was a candidate gene for engineering anthocyanin biosynthetic pathway. PMID:28293252
Violet to black pigmentation of eggplant (Solanum melongena) fruit is attributed to anthocyanin accumulation. Model systems support the interaction of biosynthetic and regulatory genes for anthocyanin biosynthesis. Anthocyanin structural gene transcription requires the expression of at least one m...
Kovinich, Nik; Kayanja, Gilbert; Chanoca, Alexandra; Otegui, Marisa S; Grotewold, Erich
Anthocyanins are induced in plants in response to abiotic stresses such as drought, high salinity, excess light, and cold, where they often correlate with enhanced stress tolerance. Numerous roles have been proposed for anthocyanins induced during abiotic stresses including functioning as ROS scavengers, photoprotectants, and stress signals. We have recently found different profiles of anthocyanins in Arabidopsis (Arabidopsis thaliana) plants exposed to different abiotic stresses, suggesting that not all anthocyanins have the same function. Here, we discuss these findings in the context of other studies and show that anthocyanins induced in Arabidopsis in response to various abiotic stresses have different localizations at the organ and tissue levels. These studies provide a basis to clarify the role of particular anthocyanin species during abiotic stress. PMID:26179363
He, Jian; Giusti, M Monica
Anthocyanins are flavonoids in fruits and vegetables that render them vivid red to blue. To date, there have been more than 635 anthocyanins identified in nature, featuring six common aglycones and various types of glycosylations and acylations. Dietary consumption of anthocyanins is high compared to other flavonoids, owing to their wide distribution in plant materials. Based upon many cell-line studies, animal models, and human clinical trials, it has been suggested that anthocyanins possess anti-inflammatory and anti-carcinogenic activity, cardiovascular disease prevention, obesity control, and diabetes alleviation properties, all of which are more or less associated with their potent antioxidant property. Evidence suggests that absorption of anthocyanins occurs in the stomach and small intestine. Epithelial tissue uptake seems to be highly efficient, yet transportation into circulation, tissue distribution, and urine excretion are very limited. The bioactivity of bioavailable anthocyanins should be a focus of future research regarding their putative health-promoting effects.
Total anthocyanins in different cultivars of mulberry were measured and a process for the industrial preparation of mulberry anthocyanins as a natural food colorant was studied. In 31 cultivars of mulberry, the total anthocyanins, calculated as cyanidin 3-glucoside, ranged from 147.68 to 2725.46 mg/L juice. Extracting and purifying with macroporous resins was found to be an efficient potential method for the industrial production of mulberry anthocyanins as a food colorant. Of six resins tested, X-5 demonstrated the best adsorbent capability for mulberry anthocyanins (91 mg/mL resin). The adsorption capacity of resins increased with the surface area and the pore radius. Residual mulberry fruit juice after extraction of pigment retained most of its nutrients, except for anthocyanins, and may provide a substrate for further processing. PMID:15577197
Montefiori, Mirco; Comeskey, Daniel J; Wohlers, Mark; McGhie, Tony K
Red-fleshed fruit occur in a small number of distantly related taxa in different sections of the genus Actinidia (kiwifruit). We describe and identify the anthocyanin profile of fruit of several Actinidia species. Differences in the relative amounts of cyanidin- and delphinidin-based anthocyanins determine whether the fruit appear red or purple. Cyanidin derivatives have been found in all Actinidia species that contain anthocyanins, whereas delphinidin derivatives are limited to two taxa: A. melanandra and A. arguta var. purpurea . The fruit of these not only contain a wider range of anthocyanins, but they also have greater concentrations. Anthocyanins of most Actinidia species are usually conjugated with either xylosyl-galactose or galactose, whereas A. deliciosa anthocyanins are conjugated with glucose and galactose.
Srivastava, Jyoti; Vankar, Padma S
In this study the red flowers of Canna indica (Cannaceae) were extracted by using sonicator and isolation of anthocyanins have been carried out. Four anthocyanin pigments have been isolated apart from quercetin and lycopene. They are Cyanidin-3-O-(6''-O-α-rhamnopyranosyl)-β-glucopyranoside (1), Cyanidin-3-O-(6''-O-α-rhamnopyranosyl)-β-galactopyranoside (2), Cyanidin-3-O-β-glucopyranoside (3) and Cyanidin-O-β-galactopyranoside (4). These compounds were isolated by using HPLC and their structures were subsequently determined on the basis of spectroscopic analyses, i.e., (1)H NMR, (13)C NMR, HMQC, HMBC, ESI-MS, FTIR, UV-Visible etc. The isolated compounds showed good antioxidant activity thus makes it suitable for use in food coloration and as a nutraceutical. Thus it is a promising pigment source for food applications.
Silva, S; Costa, E M; Calhau, C; Morais, R M; Pintado, M E
Anthocyanins have gathered the attention of the scientific community mostly due to their vast range of possible applications. They have been the center point of the research in many different fields, among which is food development, where their innate coloring, antioxidant capacity, and biological potential open interesting venues to the development of new food additives and functional foodstuffs. As the range of application grows, so does the necessity to obtain these compounds, and since they are naturally occurring, the most common way to obtain anthocyanins is to extract them from different plant sources, such as fruits and flowers. Several efforts have been made to develop methods that allow for better extraction yields and higher purification rates therefore this review aims to compile the information regarding extraction and purification procedures in a comprehensive manner.
Terahara, N; Takeda, Y; Nesumi, A; Honda, T
Three anthocyanins were isolated from the leaves of red flower tea (Benibana-cha), Camellia sinensis, and their structures were determined by means of chemical and spectroscopic analyses. Two are the anthocyanins, delphinidin and cyanidin 3-O-beta-D-galactosides, respectively. Whereas the third, delphinidin 3-0-beta-D-(6-(E)-p-coumaryl)galactopyranoside. The anthocyanins were also contained in the flowers of Benibana-cha in different compositions.
Fleschhut, Jens; Kratzer, Frank; Rechkemmer, Gerhard; Kulling, Sabine E
Anthocyanins, which are found in high concentrations in fruit and vegetable, may play a beneficial role in retarding or reversing the course of chronic degenerative diseases. However, little is known about the biotransformation and the metabolism of anthocyanins so far. The aim of the study was to investigate possible transformation pathways of anthocyanins by human faecal microflora and by rat liver microsomes as a source of cytochrome P450 enzymes as well as of glucuronyltransferases. Pure anthocyanins, an aqueous extract of red radish as well as the assumed degradation products were incubated with human faecal suspension. The incubation mixtures were purified by solid-phase extraction and analysed by HPLC/DAD/MS and GC/MS. Quantification was done by the external standard method. Furthermore the biotransformation of anthocyanins by incubation with rat liver microsomes in the presence of the cofactor NADPH (as a model for the phase I oxidation) and in the presence of activated glucuronic acid (as a model for the phase II glucuronidation) was investigated. Glycosylated and acylated anthocyanins were rapidly degraded by the intestinal microflora after anaerobic incubation with a human faecal suspension. The major stable products of anthocyanin degradation are the corresponding phenolic acids derived from the B-ring of the anthocyanin skeleton. Anthocyanins were not metabolised by cytochrome P450 enzymes, neither hydroxylated nor demethylated. However they were glucuronidated by rat liver microsomes to several products. The gut microflora seem to play an important role in the biotransformation of anthocyanins. A rapid degradation could be one major reason for the poor bioavailability of anthocyanins in pharmacokinetic studies described so far in the literature. The formation of phenolic acids as the major stable degradation products gives an important hint to the fate of anthocyanins in vivo.
Emoto, Yuko; Yoshizawa, Katsuhiko; Kinoshita, Yuichi; Yuki, Michiko; Yuri, Takashi; Yoshikawa, Yutaka; Sayama, Kazutoshi; Tsubura, Airo
Although green tea is considered to be a healthy beverage, hepatotoxicity associated with the consumption of green tea extract has been reported. In the present study, we characterized the hepatotoxicity of green tea extract in rats and explored the responsible mechanism. Six-week-old IGS rats received a single intraperitoneal (ip) injection of 200 mg/kg green tea extract (THEA-FLAN 90S). At 8, 24, 48 and 72 hrs and 1 and 3 months after exposure, liver damage was assessed by using blood-chemistry, histopathology, and immunohistochemistry to detect cell death (TUNEL and caspase-3) and proliferative activity (PCNA). Analyses of malondialdehyde (MDA) in serum and the liver and of MDA and thymidine glycol (TG) by immunohistochemistry, as oxidative stress markers, were performed. Placental glutathione S-transferase (GST-P), which is a marker of hepatocarcinogenesis, was also immunohistochemically stained. To examine toxicity at older ages, 200 mg/kg green tea extract was administered to 18-wk-old female rats. In 6-wk-old rats, 12% of males and 50% of females died within 72 hrs. In 18-wk-old rats, 88% died within 72 hrs. The serum levels of aspartate aminotransferase, alanine aminotransferase and/or total bilirubin increased in both males and females. Single-cell necrosis with positive signs of TUNEL and caspase-3 was seen in perilobular hepatocytes from 8 hrs onward in all lobular areas. PCNA-positive hepatocytes increased at 48 hrs. MDA levels in the serum and liver tended to increase, and MDA- and TG-positive hepatocytes were seen immunohistochemically. GST-P-positive hepatocellular altered foci were detected in one female rat at the 3-month time point. In conclusion, a single injection of green tea extract induced acute and severe hepatotoxicity, which might be associated with lipid peroxidation and DNA oxidative stress in hepatocytes.
Albert, Nick W; Lewis, David H; Zhang, Huaibi; Irving, Louis J; Jameson, Paula E; Davies, Kevin M
The Lc petunia system, which displays enhanced, light-induced vegetative pigmentation, was used to investigate how high light affects anthocyanin biosynthesis, and to assess the effects of anthocyanin pigmentation upon photosynthesis. Lc petunia plants displayed intense purple anthocyanin pigmentation throughout the leaves and stems when grown under high-light conditions, yet remain acyanic when grown under shade conditions. The coloured phenotypes matched with an accumulation of anthocyanins and flavonols, as well as the activation of the early and late flavonoid biosynthetic genes required for flavonol and anthocyanin production. Pigmentation in Lc petunia only occurred under conditions which normally induce a modest amount of anthocyanin to accumulate in wild-type Mitchell petunia [Petunia axillaris x (Petunia axillaris x Petunia hybrida cv. 'Rose of Heaven')]. Anthocyanin pigmentation in Lc petunia leaves appears to screen underlying photosynthetic tissues, increasing light saturation and light compensation points, without reducing the maximal photosynthetic assimilation rate (A(max)). In the Lc petunia system, where the bHLH factor Leaf colour is constitutively expressed, expression of the bHLH (Lc) and WD40 (An11) components of the anthocyanin regulatory system were not limited, suggesting that the high-light-induced anthocyanin pigmentation is regulated by endogenous MYB transcription factors.
Hale, K L; McGrath, S P; Lombi, E; Stack, S M; Terry, N; Pickering, I J; George, G N; Pilon-Smits, E A
To elucidate plant mechanisms involved in molybdenum (Mo) sequestration and tolerance, Brassica spp. seedlings were supplied with molybdate, and the effects on plant physiology, morphology, and biochemistry were analyzed. When supplied with (colorless) molybdate Indian mustard (Brassica juncea) seedlings accumulated water-soluble blue crystals in their peripheral cell layers. Energy dispersive x-ray analysis showed that Mo accumulated predominantly in the vacuoles of the epidermal cells. Therefore, the blue crystals are likely to be a Mo compound. The x-ray absorption spectrum of the plant-accumulated Mo was different than that for molybdate, indicating complexation with a plant molecule. Because the blue compound was water soluble and showed a pH-dependent color change, possible involvement of anthocyanins was investigated. An anthocyanin-less mutant of Brassica rapa ("fast plants") was compared with varieties containing normal or high anthocyanin levels. The anthocyanin-less mutant did not show accumulation of a blue compound when supplied with molybdate. In the anthocyanin-containing varieties, the blue compound colocalized with anthocyanins in the peripheral cell layers. Mo accumulation by the three B. rapa varieties was positively correlated with anthocyanin content. Addition of molybdate to purified B. rapa anthocyanin resulted in an in vitro color change from pink to blue. Therefore, Mo appears to be sequestered in vacuoles of the peripheral cell layers of Brassica spp. as a blue compound, probably a Mo-anthocyanin complex.
Albert, Nick W.; Lewis, David H.; Zhang, Huaibi; Irving, Louis J.; Jameson, Paula E.; Davies, Kevin M.
The Lc petunia system, which displays enhanced, light-induced vegetative pigmentation, was used to investigate how high light affects anthocyanin biosynthesis, and to assess the effects of anthocyanin pigmentation upon photosynthesis. Lc petunia plants displayed intense purple anthocyanin pigmentation throughout the leaves and stems when grown under high-light conditions, yet remain acyanic when grown under shade conditions. The coloured phenotypes matched with an accumulation of anthocyanins and flavonols, as well as the activation of the early and late flavonoid biosynthetic genes required for flavonol and anthocyanin production. Pigmentation in Lc petunia only occurred under conditions which normally induce a modest amount of anthocyanin to accumulate in wild-type Mitchell petunia [Petunia axillaris×(Petunia axillaris×Petunia hybrida cv. ‘Rose of Heaven’)]. Anthocyanin pigmentation in Lc petunia leaves appears to screen underlying photosynthetic tissues, increasing light saturation and light compensation points, without reducing the maximal photosynthetic assimilation rate (Amax). In the Lc petunia system, where the bHLH factor Leaf colour is constitutively expressed, expression of the bHLH (Lc) and WD40 (An11) components of the anthocyanin regulatory system were not limited, suggesting that the high-light-induced anthocyanin pigmentation is regulated by endogenous MYB transcription factors. PMID:19380423
Syamaladevi, Roopesh M; Andrews, Preston K; Davies, Neal M; Walters, Thomas; Sablani, Shyam S
Consumer demand for products rich in phytochemicals is increasing as a result of greater awareness of their potential health benefits. However, processed products are stored for long-term and the phytochemicals are susceptible to degradation during storage. The objective of this study was to assess the storage effects on phytochemicals in thermally processed blueberries. Thermally processed canned berries and juice/puree were analysed for phytochemicals during their long-term storage. The phytochemical retention of thermally processed blueberries during storage was not influenced by production system (conventional versus organic). During 13 months of storage, total anthocyanins, total phenolics and total antioxidant activity in canned blueberry solids decreased by up to 86, 69 and 52% respectively. In canned blueberry syrup, total anthocyanins and total antioxidant activity decreased by up to 68 and 15% respectively, while total phenolic content increased by up to 117%. Similar trends in phytochemical content were observed in juice/puree stored for 4 months. The extent of changes in phytochemicals of thermally processed blueberries during storage was significantly influenced by blanching. Long-term storage of thermally processed blueberries had varying degrees of influence on degradation of total anthocyanins, total phenolics and total antioxidant activity. Blanching before thermal processing helped to preserve the phytochemicals during storage of blueberries. Copyright © 2011 Society of Chemical Industry.
Goufo, Piebiep; Trindade, Henrique
Epidemiological studies suggested that the low incidence of certain chronic diseases in rice-consuming regions of the world might be associated with the antioxidant compound contents of rice. The molecules with antioxidant activity contained in rice include phenolic acids, flavonoids, anthocyanins, proanthocyanidins, tocopherols, tocotrienols, γ-oryzanol, and phytic acid. This review provides information on the contents of these compounds in rice using a food composition database built from compiling data from 316 papers. The database provides access to information that would have otherwise remained hidden in the literature. For example, among the four types of rice ranked by color, black rice varieties emerged as those exhibiting the highest antioxidant activities, followed by purple, red, and brown rice varieties. Furthermore, insoluble compounds appear to constitute the major fraction of phenolic acids and proanthocyanidins in rice, but not of flavonoids and anthocyanins. It is clear that to maximize the intake of antioxidant compounds, rice should be preferentially consumed in the form of bran or as whole grain. With respect to breeding, japonica rice varieties were found to be richer in antioxidant compounds compared with indica rice varieties. Overall, rice grain fractions appear to be rich sources of antioxidant compounds. However, on a whole grain basis and with the exception of γ-oryzanol and anthocyanins, the contents of antioxidants in other cereals appear to be higher than those in rice.
Santacruz, Liliana; Carriazo, José G; Almanza, Ovidio; Osorio, Coralia
The qualitative and quantitative anthocyanin composition of four wild tropical fruits from Colombia was studied. Compounds of "mora pequeña" ( Rubus megalococcus Focke.), "uva de árbol" ( Myrciaria aff. cauliflora O. Berg), coral, and motilón ( Hyeronima macrocarpa Mull. Arg.) fruits were separately extracted with methanol-acetic acid (95:5, v/v). The anthocyanin-rich extracts (AREs) were obtained by selective adsorption on Amberlite XAD-7. Each extract was analyzed by HPLC-PDA and HPLC-HRESI-MS(n) with LCMS-IT-TOF equipment in order to characterize the anthocyanin pigments and the coinjection in HPLC using standards allowed identifying the major constituents in each extract. The antioxidant activity was measured by electron paramagnetic resonance (EPR) and UV-vis spectroscopy, using ABTS and DPPH free radicals. The ARE of motilón ( H. macrocarpa Müll. Arg) exhibited the highest radical scavenging activity in comparison to the other extracts. A second-order kinetic model was followed in all of the cases. These results suggested that the studied fruits are promising not only as source of natural pigments but also as antioxidant materials for food industry.
Cisowska, Agnieszka; Wojnicz, Dorota; Hendrich, Andrzej B
Anthocyanins are particularly abundant in different fruits, especially in berries. The beneficial effects of these compounds for human health have been known from at least the 16th century. Despite the great number of papers devoted to the different biological effects exerted by anthocyanins only a limited number of studies is focused on the antimicrobial activity of these compounds. Anthocyanin content of berry fruits varies from 7.5 mg/100 mg fresh fruit in redcurrant (Ribes rubum) up to 460 mg/100 g fresh fruit in chokeberry (Aronia melanocarpa). After consumption, anthocyanins are intensively metabolized, mainly in the intestines and liver. Glucorination, methylation and sulfation are the most typical metabolic reactions. Antimicrobial activity of crude extracts of plant phenolic compounds against human pathogens has been intensively studied to characterize and develop new healthy food ingredients as well as medical and pharmaceutical products. However, there is very little information available about the antimicrobial activity of the pure anthocyanins. In the last part of this review we present the collection of papers describing the anthocyanin profiles of different fruits (mainly berries) and the antimicrobial properties of the identified compounds. Generally, anthocyanins are active against different microbes, however Gram-positive bacteria usually are more susceptible to the anthocyanin action than Gram-negative ones. Mechanisms underlying anthocyanin activity include both membrane and intracellular interactions of these compounds. Antimicrobial activity of berries and other anthocyanin-containing fruits is likely to be caused by multiple mechanisms and synergies because they contain various compounds including anthocyanins, weak organic acids, phenolic acids, and their mixtures of different chemical forms. Therefore, the antimicrobial effect of chemically complex compounds has to be critically analyzed.
Aguilera, Yolanda; Mojica, Luis; Rebollo-Hernanz, Miguel; Berhow, Mark; de Mejía, Elvira González; Martín-Cabrejas, María A
Anthocyanin-rich powders and aqueous extracts, with high antioxidant activities, were obtained from black bean seed coats and applied to colour a sport beverage. Idaho and Otomi bean coats were extracted in water-citric acid 2% (1/50, w/v), stirring for 4h at 40°C. Anthocyanins from Idaho and Otomi extracts (1.83mg and 1.02mg C3G/g, respectively) were applied to a commercially available sport beverage, with and without 2% β-cyclodextrin (βCD) under light and darkness conditions for 10days, and stored at 4°C and 25°C for 6weeks. At different light and storage conditions, anthocyanin degradation fitted a first-order reaction model. All bean coat anthocyanins combined with βCD showed extended half-life (up to 13months), higher D-values (up to 43months) and fewer differences in colourimetric properties (lightness, chroma and hue angle) under darkness and 4°C conditions. These black bean coat aqueous extracts and powders might represent natural alternatives to synthetic colorants, ecologically extracted, and with a high antioxidant potential.
Anthocyanins are water soluble plant secondary metabolites responsible for the blue, purple, and red color of many plant tissues. They have been shown to be strong antioxidants, and may exert a wide range of health benefits through antioxidant or other mechanisms. Anthocyanins occur primarily as gly...
Anthocyanins are water soluble plant secondary metabolites responsible for the blue, purple, and red color of many plant tissues. They have been shown to be strong antioxidants, and may exert a wide range of health benefits through antioxidant or other mechanisms. Anthocyanins occur primarily as g...
Kohno, Yoshiumi; Haga, Eriko; Yoda, Keiko; Shibata, Masashi; Fukuhara, Choji; Tomita, Yasumasa; Maeda, Yasuhisa; Kobayashi, Kenkichiro
Because of its non-toxicity, naturally occurring anthocyanin is potentially suitable as a colorant for foods and cosmetics. To the wider use of the anthocyanin, the immobilization on the inorganic host for an easy handling as well as the improvement of the stability is required. This study is focused on the adsorption of significant amount of the natural anthocyanin dye onto mesoporous silica, and on the stability enhancement of the anthocyanin by the complexation. The anthocyanin has successfully been adsorbed on the HMS type mesoporous silica containing small amount of aluminum. The amount of the adsorbed anthocyanin has been increased by modifying the pore wall with n-propyl group to make the silica surface hydrophobic. The light fastness of the adsorbed anthocyanin has been improved by making the composite with the HMS samples containing aluminum, although the degree of the improvement is not so large. It has been proposed that incorporation of the anthocyanin molecule deep inside the mesopore is required for the further enhancement of the stability.
Partial cDNA fragments of Myb, Myc, Wd, Chs and Dfr genes were generated by Reverse Transcription-PCR using total RNA isolated from flowers of P. amabilis (L.) Blume (anthocyanin-free) and P. schilleriana Rchb. f. (anthocyanin-containing) and cloned into a TOPO vector. RT-PCR revealed that the struc...
Ajiboye, Taofeek O; Salawu, Nasir A; Yakubu, Musa T; Oladiji, Adenike T; Akanji, Musbau A; Okogun, Joseph I
The antioxidant and drug metabolizing potentials of Hibiscus anthocyanin extract in CCl(4)- induced oxidative damage of rat liver was investigated. Hibiscus anthocyanin extract effectively scavenge α-diphenyl-β-picrylhydrazyl (DPPH) radical, superoxide ion, and hydrogen peroxide. It produced a 92% scavenging effect of DPPH radical at a concentration of 2.0 mg/mL. Hibiscus anthocyanin extract produced a 69 and 90% scavenging effect on superoxide ion and hydrogen peroxide, respectively, at 1.0 mg/mL, which compared favorably with the synthetic antioxidant (butylated hydroanisole and α-tocopherol). A reducing power of this anthocyanin was examined using K(3)Fe(CN)(6). Hibiscus anthocyanin extract has reducing power that is approximately 2-fold that of the synthetic antioxidant, butylated hydroanisole. Hibiscus anthocyanin extract produced a significantly increase and completely attenuated the CCl(4)-mediated decrease in antioxidant enzymes (e.g., catalase, superoxide dismutase, glutathione peroxidase, and glutathione reductase). However, the level of nonenzymic antioxidant molecules (i.e., vitamins C and E) were significant preserved by Hibiscus anthocyanin extract. There was an induction of phase II drug-detoxifying enzymes: glutathione S-transferase, NAD(H):quinone oxidoreductase, and uridyl diphosphoglucuronosyl transferase by 65, 45, and 57%, respectively. In view of these properties, Hibiscus sabdariffa anthocyanin extract can act as a prophylactic by intervening as a free radical scavenger both in vitro and in vivo as well as inducing the phase II drug detoxification enzymes.
Xu, Lianji; Choi, Tae Hyun; Kim, Sukwha; Kim, Sang-Hyon; Chang, Hyuk Won; Choe, Misun; Kwon, Sun Young; Hur, Ji An; Shin, Sung Chul; Chung, Jong Il; Kang, Dawon; Zhang, Duo
Anthocyanins are known to have antioxidant and antiinflammatory effects. We hypothesized that anthocyanins would enhance wound healing in Sprague-Dawley rats. The purpose of this study was to evaluate our hypothesis and investigate the mechanism of wound healing enhancement. The cytoprotective effect of an immortalized epidermal keratinocyte cell line (HaCaT) and human neonatal dermal fibroblasts in response to various concentrations of anthocyanins was determined. Vascular endothelial growth factor (VEGF) and thrombospondin 1 (TSP1) of HaCaT were measured by Western blot analysis. Anthocyanins were applied to the wounds in rats, and the healing ratio was calculated. Tissue VEGF, TSP1, CD31, nuclear factor-κB, and phosphorylation of IκBα were measured. The viability of the HaCaT cell line and human neonatal dermal fibroblasts increased under cytotoxicity by H2O2 in the anthocyanin-treated groups. The VEGF in the anthocyanin-treated groups increased, whereas TSP1 decreased. Wounds in the experimental groups healed faster, and VEGF and CD31 increased in the experimental groups, whereas TSP1 decreased. Anthocyanins inhibited the translocation of nuclear factor-κB (p65) from cytosol to nucleus and also prevented the phosphorylation of IκBα. Anthocyanins enhance wound healing through a cytoprotective effect, enhancement of angiogenesis, and an antiinflammatory effect.
Scalzo, Jessica; Stevenson, David; Hedderley, Duncan
This study compares the yields, weights and anthocyanin contents of fruit from a group of seven new cultivars released from the New Zealand blueberry breeding programme and selected for the longest possible combined harvest season. The measured factors were primarily influenced by cultivar, and seasonal variations had relatively minor effects. The late-ripening cultivars 'Velluto Blue' and 'Centra Blue' had the highest fruit yields, anthocyanin contents and estimated total anthocyanin harvestable from a given area. 'Blue Moon' and 'Sky Blue' had the largest fruit sizes. The early-ripening cultivars 'Blue Bayou', 'Blue Moon' and 'Sunset Blue' had the lowest anthocyanin contents. The yield, fruit size and total anthocyanin content results obtained from any single year were highly correlated with the average of the three years, which makes pursuing the evaluation for these traits from a single year and at an early stage of plant development a practical proposition. Copyright © 2013 Elsevier Ltd. All rights reserved.
Enoki, Shinichi; Hattori, Tomoki; Ishiai, Shiho; Tanaka, Sayumi; Mikami, Masachika; Arita, Kayo; Nagasaka, Shu; Suzuki, Shunji
We investigated the effect of vanillylacetone (VA) on anthocyanin accumulation with aim of improving grape berry coloration. Spraying Vitis vinifera cv. Muscat Bailey A berries with VA at veraison increased sugar/acid ratio, an indicator of maturation and total anthocyanin accumulation. To elucidate the molecular mechanism underlying the effect of VA on anthocyanin accumulation, in vitro VA treatment of a grapevine cell culture was carried out. Endogenous abscisic acid (ABA) content was higher in the VA-treated cell cultures than in control at 3h after treatment. Consistent with this, the relative expression levels of anthocyanin-synthesis-related genes, including DFR, LDOX, MybA1 and UFGT, in VA-treated cell cultures were much higher than those in control, and high total anthocyanin accumulation was noted in the VA-treated cell cultures as well. These results suggest that VA up-regulates the expression of genes leading to anthocyanin accumulation by inducing endogenous ABA. In addition, VA increased total anthocyanin content in a dose-dependent manner. Although VA treatment in combination with exogenous ABA did not exhibit any synergistic effect, treatment with VA alone showed an equivalent effect to that with exogenous ABA alone on total anthocyanin accumulation. These findings point to the possibility of using VA for improving grape berry coloration. Copyright © 2017 Elsevier GmbH. All rights reserved.
Sriarj, Wannakorn; Aoki, Kazuhiro; Ohya, Keiichi; Takahashi, Mariko; Takagi, Yuzo; Shimokawa, Hitoyata
Previously, we have demonstrated that the extracellular matrix from dentin affects osteoclastic activity in co-culture between osteoclast and osteoblast-rich fraction from mouse marrow cells. In the present study, we aimed to investigate the mechanisms of dentin matrix extract-induced osteoclastogenesis in mouse bone marrow macrophages (BMMs). Dentin proteins were extracted from bovine incisor root dentin using 0.6 M HCl. BMMs were cultured in α-MEM containing macrophage colony-stimulating factor/receptor activator of nuclear factor kappa-B ligand in the presence or absence of dentin matrix extract. Tartrate-resistant acid phosphatase (TRAP)-positive cell number, total TRAP activity, and the mRNA levels of osteoclast-related genes, assayed by real-time RT-PCR, were determined as markers of osteoclastogenesis. A neutralizing antibody against transforming growth factor-β1 (TGF-β1), SB431542, a TGF-β receptor inhibitor, and ELISA were used to determine the role of TGF-β1. We observed increases in TRAP-positive cell number, TRAP activity, and the mRNA levels of osteoclast-related genes of BMMs cultured with dentin extract. The use of a neutralizing antibody against TGF-β1 or SB431542 inhibited the inductive effect of dentin extract, suggesting TGF-β1 involvement. The addition of exogenous TGF-β1, but not bone morphogenic protein-2, also increased osteoclastogenesis, corresponding to the ELISA determination of TGF-β1 in the dentin extract. In conclusion, our results indicate that proteins from dentin matrix have an inductive effect in osteoclastogenesis, which is mediated, in part, by TGF-β1.
Kalt, Wilhelmina; McDonald, Jane E; Liu, Yan; Fillmore, Sherry A E
The human health benefits of anthocyanins (Anc) and other flavonoids are widely recognized. However, the flavonoid-based urinary metabolites arising in vivo after Anc intake are not well described. Human (n = 17) urine was collected while blueberry juice (BJ) was consumed daily for 28 days and once after a 7 day washout. MS/MS scanning of 664 urine samples for 18 parent Anc (PAnc) and 42 predicted Anc metabolites (AncM) yielded 371 products (i.e., MS/MS × retention time (RT)). Flavonoid-based AncM, which were likely underestimated, were almost 20 times more abundant than PAnc. Together, PAnc and AncM accounted for about 1% of the daily Anc dose. Aglycone forms were >94% of the total. Cluster analysis of the 371 Anc identified about 55 major Anc that contributed about 80% to the total Anc. The abundance of flavonoid-based Anc-derived products in the gastrointestinal tract could contribute to the health benefits of Anc-rich berries.
Anthocyanins are considered an excellent source of antioxidant phytochemicals for health benefits. The majority of wine, table and raisin grapes have anthocyanins only in their colored skin. Anthocyanin content of grapes would be increased if their flesh also contained anthocyanins. Rubired wine ...
Borges, Gina; Roowi, Suri; Rouanet, Jean-Max; Duthie, Garry G; Lean, Michael E J; Crozier, Alan
The fate of anthocyanins and ellagitannins in rats was monitored following ingestion of raspberry juice. After 1 h low nM concentrations of unmetabolised anthocyanins were present in plasma but these declined by 2 h and after 4 h they were no longer detectable. For the first 2 h there was an almost full recovery of anthocyanins as they passed from the stomach through the duodenum/jejunum and into the ileum. After 3 h less than 50% were recovered, and the levels declined rapidly thereafter. Excretion of raspberry anthocyanins in urine over a 24 h period was equivalent to 1.2% of the amount ingested. Trace quantities of anthocyanins were detected in the caecum, colon and faeces and they were absent in extracts of liver, kidneys and brain. Urine also contained a number of phenolic acids but most were present in quantities well in excess of the 918 nmol of anthocyanins present in the ingested juice. These findings indicate that raspberry anthocyanins per se are poorly absorbed, probably prior to reaching the ileum, and that substantial amounts pass from the small to the large intestine where they are degraded by colonic bacteria. Ellagitannins disappeared in the stomach without accumulation of ellagic acid.
Caramanico, Leila; Rustioni, Laura; De Lorenzis, Gabriella
Iron chlorosis is a diffuse disorder affecting Mediterranean vineyards. Beside the commonly described symptom of chlorophyll decrease, an apex reddening was recently observed. Secondary metabolites, such as anthocyanins, are often synthetized to cope with stresses in plants. The present work aimed to evaluate grapevine responses to iron deficiency, in terms of anthocyanin metabolism (reflectance spectrum, total anthocyanin content, HPLC profile and gene expression) in apical leaves of Cabernet sauvignon and Sangiovese grown in hydroponic conditions. Iron supply interruption produced after one month an increasing of anthocyanin content associated to a more stable profile in both cultivars. In Cabernet sauvignon, the higher red pigment accumulation was associated to a lower intensity of chlorotic symptoms, while in Sangiovese, despite the activation of the metabolism, the lower anthocyanin accumulation was associated to a stronger decrease in chlorophyll concentration. Gene expression data showed a significant increase of anthocyanin biosynthesis. The effects on the expression of structural and transcription factor genes of phenylpropanoid pathway were cultivar dependent. F3H, F3'H, F3'5'H and LDOX genes, in Cabernet sauvignon, and AOMT1 and AOMT genes, in Sangiovese, were positively affected by the treatment in response to iron deficiency. All data support the hypothesis of an anthocyanin biosynthesis stimulation rather than a decreased degradation of them due to iron chlorosis. Copyright © 2017 Elsevier Masson SAS. All rights reserved.
He, Xianzhi; Li, Yong; Lawson, Darlene; Xie, De-Yu
In this study, we investigate the metabolic engineering of anthocyanins in two dark tobacco crops (Narrow Leaf Madole and KY171) and evaluate the effects on physiological features of plant photosynthesis. Arabidopsis PAP1 (production of anthocyanin pigment 1) gene (AtPAP1) encodes a R2R3-type MYB transcript factor that is a master component of regulatory complexes controlling anthocyanin biosynthesis. AtPAP1 was introduced to Narrow Leaf Madole and KY171 plants. Multiple transgenic plants developed red/purple pigmentation in different tissues. Quantitative real-time polymerase chain reaction (qRT-PCR) analysis showed that the expression levels of six pathway genes were increased two- to eight-fold in AtPAP1 transgenic plants compared with vector control plants. Dihydroflavonol reductase and anthocyanidin synthase genes that were not expressed in wild-type plants were activated. Spectrophotometric measurement showed that the amount of anthocyanins in AtPAP1 transgenic plants were 400-800 µg g(-1) fresh weight (FW). High-performance liquid chromatography (HPLC) analysis showed that one main anthocyanin molecule accounted for approximately 98% of the total anthocyanins. Tandem MS/MS analysis using HPLC coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry identified the main anthocyanin as cyanidin 3-O-rutinoside, an important medicinal anthocyanin. Analysis of photosynthesis rate, chlorophylls and carotenoids contents showed no differences between red/purple transgenic and control plants, indicating that this metabolic engineering did not alter photosynthetic physiological traits. This study shows that AtPAP1 is of significance for metabolic engineering of anthocyanins in crop plants for value-added traits.
Schweiggert, Ralf M; Vargas, Ester; Conrad, Jürgen; Hempel, Judith; Gras, Claudia C; Ziegler, Jochen U; Mayer, Angelika; Jiménez, Víctor; Esquivel, Patricia; Carle, Reinhold
Pigment profiles of yellow-, orange-, and red-peeled cashew (Anacardium occidentale L.) apples were investigated. Among 15 identified carotenoids and carotenoid esters, β-carotene, and β-cryptoxanthin palmitate were the most abundant in peels and pulp of all samples. Total carotenoid concentrations in the pulp of yellow- and red-peeled cashew apples were low (0.69-0.73 mg/100g FW) compared to that of orange-peeled samples (2.2mg/100g FW). The color difference between the equally carotenoid-rich yellow and red colored samples indicated the presence of a further non-carotenoid pigment type in red peels. Among four detected anthocyanins, the major anthocyanin was unambiguously identified as 7-O-methylcyanidin 3-O-β-D-galactopyranoside by NMR spectroscopy. Red and yellow peel color was chiefly determined by the presence and absence of anthocyanins, respectively, while the orange appearance of the peel was mainly caused by increased carotenoid concentrations. Thus, orange-peeled fruits represent a rich source of provitamin A (ca. 124 μg retinol-activity-equivalents/100g pulp, FW).
Park, Nam Il; Xu, Hui; Li, Xiaohua; Jang, In Hyuk; Park, Suhyoung; Ahn, Gil Hwan; Lim, Yong Pyo; Kim, Sun Ju; Park, Sang Un
Radish [Raphanus sativus (Rs)] is an important dietary vegetable in Asian countries, especially China, Japan, and Korea. To elucidate the molecular mechanisms of anthocyanin accumulation in radish, the gene expression of enzymes directly involved in anthocyanin biosynthesis was analyzed. These genes include phenylalanine ammonia lyase (PAL), cinnamate 4-hydroxylase (C4H), 4-coumarate-CoA ligase (4CL), chalcone synthase (CHS), chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), dihydroflavonol reductase (DFR), and anthocyanidin synthase (ANS). RsDFR and RsANS were found to accumulate in the flesh or skin of two radish cultivars (Man Tang Hong and Hong Feng No.1). Radish skin contained higher CHS, CHI, and F3H transcript levels than radish flesh in all three cultivars. In the red radish, 16 anthocyanins were separated and identified by high-performance liquid chromatography (HPLC) and elctrospray ionization-tandem mass spectrometry (ESI-MS/MS). Some of them were acylated with coumaroyl, malonoyl, feruoyl, and caffeoyl moieties. Furthermore (-)-epicatechin and ferulic acid were also identified in the three cultivars.
Rinaldo, Amy R; Cavallini, Erika; Jia, Yong; Moss, Sarah M A; McDavid, Debra A J; Hooper, Lauren C; Robinson, Simon P; Tornielli, Giovanni B; Zenoni, Sara; Ford, Christopher M; Boss, Paul K; Walker, Amanda R
Anthocyanins are flavonoid compounds responsible for red/purple colors in the leaves, fruit, and flowers of many plant species. They are produced through a multistep pathway that is controlled by MYB transcription factors. VvMYBA1 and VvMYBA2 activate anthocyanin biosynthesis in grapevine (Vitis vinifera) and are nonfunctional in white grapevine cultivars. In this study, transgenic grapevines with altered VvMYBA gene expression were developed, and transcript analysis was carried out on berries using a microarray technique. The results showed that VvMYBA is a positive regulator of the later stages of anthocyanin synthesis, modification, and transport in cv Shiraz. One up-regulated gene, ANTHOCYANIN 3-O-GLUCOSIDE-6″-O-ACYLTRANSFERASE (Vv3AT), encodes a BAHD acyltransferase protein (named after the first letter of the first four characterized proteins: BEAT [for acetyl CoA:benzylalcohol acetyltransferase], AHCT [for anthocyanin O-hydroxycinnamoyltransferase], HCBT [for anthranilate N-hydroxycinnamoyl/benzoyltransferase], and DAT [for deacetylvindoline 4-O-acetyltransferase]), belonging to a clade separate from most anthocyanin acyltransferases. Functional studies (in planta and in vitro) show that Vv3AT has a broad anthocyanin substrate specificity and can also utilize both aliphatic and aromatic acyl donors, a novel activity for this enzyme family found in nature. In cv Pinot Noir, a red-berried grapevine mutant lacking acylated anthocyanins, Vv3AT contains a nonsense mutation encoding a truncated protein that lacks two motifs required for BAHD protein activity. Promoter activation assays confirm that Vv3AT transcription is activated by VvMYBA1, which adds to the current understanding of the regulation of the BAHD gene family. The flexibility of Vv3AT to use both classes of acyl donors will be useful in the engineering of anthocyanins in planta or in vitro. © 2015 American Society of Plant Biologists. All Rights Reserved.
Rinaldo, Amy R.; Cavallini, Erika; Jia, Yong; Moss, Sarah M.A.; McDavid, Debra A.J.; Hooper, Lauren C.; Robinson, Simon P.; Tornielli, Giovanni B.; Zenoni, Sara; Ford, Christopher M.; Boss, Paul K.; Walker, Amanda R.
Anthocyanins are flavonoid compounds responsible for red/purple colors in the leaves, fruit, and flowers of many plant species. They are produced through a multistep pathway that is controlled by MYB transcription factors. VvMYBA1 and VvMYBA2 activate anthocyanin biosynthesis in grapevine (Vitis vinifera) and are nonfunctional in white grapevine cultivars. In this study, transgenic grapevines with altered VvMYBA gene expression were developed, and transcript analysis was carried out on berries using a microarray technique. The results showed that VvMYBA is a positive regulator of the later stages of anthocyanin synthesis, modification, and transport in cv Shiraz. One up-regulated gene, ANTHOCYANIN 3-O-GLUCOSIDE-6″-O-ACYLTRANSFERASE (Vv3AT), encodes a BAHD acyltransferase protein (named after the first letter of the first four characterized proteins: BEAT [for acetyl CoA:benzylalcohol acetyltransferase], AHCT [for anthocyanin O-hydroxycinnamoyltransferase], HCBT [for anthranilate N-hydroxycinnamoyl/benzoyltransferase], and DAT [for deacetylvindoline 4-O-acetyltransferase]), belonging to a clade separate from most anthocyanin acyltransferases. Functional studies (in planta and in vitro) show that Vv3AT has a broad anthocyanin substrate specificity and can also utilize both aliphatic and aromatic acyl donors, a novel activity for this enzyme family found in nature. In cv Pinot Noir, a red-berried grapevine mutant lacking acylated anthocyanins, Vv3AT contains a nonsense mutation encoding a truncated protein that lacks two motifs required for BAHD protein activity. Promoter activation assays confirm that Vv3AT transcription is activated by VvMYBA1, which adds to the current understanding of the regulation of the BAHD gene family. The flexibility of Vv3AT to use both classes of acyl donors will be useful in the engineering of anthocyanins in planta or in vitro. PMID:26395841
Sozański, Tomasz; Kucharska, Alicja Z; Rapak, Andrzej; Szumny, Dorota; Trocha, Małgorzata; Merwid-Ląd, Anna; Dzimira, Stanisław; Piasecki, Tomasz; Piórecki, Narcyz; Magdalan, Jan; Szeląg, Adam
Cardiovascular benefits of fruits are attributed mainly to their (poly)phenolic constituents, especially anthocyanins. The main aim of our study is to compare effects of iridoids and anthocyanins from one fruit on diet-induced atherosclerosis. The cornelian cherry is a native or cultivated plant that grows in many European countries, used in cuisine and folk medicine. In our previous study, we showed its constituents and proved that oral administration of lyophilized fruits to hypercholesterolemic rabbits had preventive effects on atherosclerosis through the activation of PPARα expression. In this study, we have compared the effects of the main constituents of the cornelian cherry:iridoid loganic acid and anthocyanins. Our experiment followed the model used in our previous study, in which rabbits were fed 1% cholesterol. We showed that both loganic acid (20 mg/kg b.w.) and a mixture of anthocyanins (10 mg/kg b.w.) administered orally for 60 days had a positive impact on dyslipidemia caused by cholesterol-rich diet, although the effects of anthocyanins were more pronounced. Anthocyanins decreased total and LDL-cholesterol and triglycerides and increased HDL-cholesterol. Loganic acid showed similar effects, but only the triglycerides and HDL-cholesterol changes achieved statistical significance. Anthocyanins, and to a lesser extent loganic acid, significantly decreased intima thickness and intima/media ratio in the thoracic aorta. Both substances decrease ox-LDL in the plasma. Anthocyanins significantly increased expression of PPARγ and α in the liver. Loganic acid also increased their expression, but to a lesser extent. Conversely, loganic acid showed pronounced anti-inflammatory effects, decreasing TNF-α and IL-6 activity. Our results imply that both substances have a positive effect on factors contributing to the development of diet-induced atherosclerosis. Our results also indicate the potential health benefits of fruits containing anthocyanins and iridoids
Sakaguchi, Yumi; Ozaki, Yukio; Miyajima, Ikuo; Yamaguchi, Masaatsu; Fukui, Yuko; Iwasa, Keiko; Motoki, Satoru; Suzuki, Takashi; Okubo, Hiroshi
Two major anthocyanins (A1 and A2) were isolated from peels of the spears of Asparagus officinalis cv. Purple Passion. They were purified by column, paper and high-performance liquid chromatographic separations, and their structures were elucidated by high-resolution Fourier transform ion cyclotron resonance mass spectrometry (HR-FT-ICR MS), 1H, 13C and two-dimensional NMR spectroscopic analyses and either acid or alkaline hydrolysis, respectively. A1 was identified as cyanidin 3-[3''-(O-beta-d-glucopyranosyl)-6''-(O-alpha-l-rhamnopyranosyl)-O-beta-d-glucopyranoside], whereas A2 was cyanidin 3-rutinoside, which is widely distributed in higher plants. Oxygen radical absorbance capacity (ORAC) assays proved their high antioxidant activities.
Nabavi, S F; Habtemariam, S; Daglia, M; Shafighi, N; Barber, A J; Nabavi, S M
Diabetic retinopathy is one of the most common complications of diabetes. A plethora of literature indicates that oxidative stress may play a central role in the pathogenesis of diabetic retinopathy. One could thus hypothesise that antioxidant therapies may be protective for diabetic retinopathy. Anthocyanins are important natural bioactive pigments responsible for red-blue colour of fruits, leaves, seeds, stems and flowers in a variety of plant species. Apart from their colours, anthocyanins are known to be health-promoting phytochemicals with potential properties useful to protect against oxidative stress in some degenerative diseases. They also have a variety of biological properties including anti-inflammatory, antibacterial, anticancer, and cardio-protective properties. Some reports further suggest a therapeutic role of anthocyanins to prevent and/or protect against ocular diseases but more studies are needed to examine their potential as alternative therapy to diabetic retinopathy. The present article reviews the available literature concerning the beneficial role of anthocyanins in diabetic retinopathy.
Yamasaki, H; Uefuji, H; Sakihama, Y
Red anthocyanin prepared from petals of Hibiscus rosa-sinensis L. was photobleached in the EDTA-riboflavin system. The rate of bleaching monitored at 565 nm depended on the light intensity and EDTA concentrations. Anaerobic conditions and/or addition of superoxide dismutase prevented the bleaching of anthocyanin, whereas mannitol and catalase did not. A similar bleaching was observed under dark conditions in the xanthine-xanthine oxidase system. The results indicate that anthocyanin is bleached by the nonenzymatic reaction with the superoxide radical and suggest that the pigment can function as an antioxidant. The antioxidative efficiency of cyanidin to superoxide was 10-fold higher than that of cyanidin-3-sophoroside as a Hibiscus anthocyanin.
Lila, Mary Ann
Anthocyanin pigments and associated flavonoids have demonstrated ability to protect against a myriad of human diseases, yet they have been notoriously difficult to study with regard to human health. Anthocyanins frequently interact with other phytochemicals to potentiate biological effects, thus contributions from individual components are difficult to decipher. The complex, multicomponent structure of compounds in a bioactive mixture and the degradation of flavonoids during harsh extraction procedures obscure the precise assignment of bioactivity to individual pigments. Extensive metabolic breakdown after ingestion complicates tracking of anthocyanins to assess absorption, bioavailability, and accumulation in various organs. Anthocyanin pigments and other flavonoids that are uniformly, predictably produced in rigorously controlled plant cell culture systems can be a great advantage for health and nutrition research because they are quickly, easily isolated, lack interferences found in whole fruits, can be elicited to provoke rapid and prolific accumulation, and are amenable to biolabeling so that metabolic fate can be investigated after ingestion. PMID:15577194
Nurmi, Tarja; Mursu, Jaakko; Heinonen, Marina; Nurmi, Anna; Hiltunen, Raimo; Voutilainen, Sari
We studied the metabolism of berry anthocyanins to phenolic acids in six human subjects by giving them bilberry-lingonberry puree with and without oat cereals. Puree + cereals contained 1435 micromol of anthocyanins and 339 micromol of phenolic acids. The urinary excretion of measured 18 phenolic acids increased 241 micromol during the 48 h follow-up after the puree + cereals supplementation. The excretion peak of dietary phenolic acids was observed at 4-6 h after the puree + cereals supplementation and 2 h earlier after the supplementation of the puree alone. Homovanillic and vanillic acids were the most abundant metabolites, and they were partly produced from anthocyanins. No gallic acid, a fragmentation product of delphinidin glycosides, was detected, and only a very low amount of malvidin glycosides was possibly metabolized to syringic acid. Although anthocyanins were partly fragmented to phenolic acids, still a large part of metabolites remained unknown.
Investigation of the mechanisms of using metal complexation and cellulose nanofiber/sodium alginate layer-by-layer coating for retaining anthocyanin pigments in thermally processed blueberries in aqueous media.
Jung, Jooyeoun; Cavender, George; Simonsen, John; Zhao, Yanyun
This study investigated the mechanisms of anthocyanin pigment retention using Fe(3+)-anthocyanin complexation and cellulose nanofiber (CNF)/sodium alginate (SA) layer-by-layer (LBL) coatings on thermally processed blueberries in aqueous media. Anthocyanin pigments were polymerized through complexation with Fe(3+) but readily degraded by heat (93 °C for 7 min) in the aqueous media because of poor stability. CNF/SA LBL coating was successful to retain anthocyanin pigments in thermally processed blueberries. Fruits coated with CNF containing CaCl2 followed by treatment in a SA bath formed a second hydrogel layer onto the CNF layer (LBL coating system) through cross-linking between Ca(2+) and alginic acid. Methyl-cellulose-modified CNF improved the interactions between CNF, the fruit surface, and the SA layer. This study demonstrated that the CNF/SA LBL coating system was effective to retain anthocyanin pigments on thermally processed whole blueberries, whereas no combined benefit of complexation with coating was observed. Results explained the mechanisms of the new approaches for developing colorful and nutritionally enhanced anthocyanin-rich fruit products.
Fogelman, Edna; Tanami, Sivan; Ginzberg, Idit
Skin color of red potatoes is due to accumulation of anthocyanins in the tuber periderm, a protective tissue that replaces the epidermis at an early stage of tuber development. The periderm consists of external layers of suberized phellem cells making up the skin, and internal layers of parenchyma-like phelloderm cells. Red pigmentation is an important marketing factor for red-skinned potatoes. However, injuries to the tuber surface, which are common in the potato industry, result in the development of a wound periderm that is devoid of the characteristic red coloration. To study the reason for these differences in anthocyanin accumulation, the expression level of anthocyanin biosynthesis genes and regulators was monitored in native and wound periderm using microarray analysis and quantitative polymerase chain reaction. We found significantly higher expression of the anthocyanin pathway in the phelloderm cells compared with the skin and tuber-flesh samples. However, in wound periderm, the anthocyanin pathway was strongly downregulated relative to the native periderm. This was true for two developmental stages of the native periderm--'immature', when the skin is prone to skinning injuries, and 'mature', following skin set--suggesting that anthocyanin synthesis continues postharvest. Wound-induced expression of steroidal glycoalkaloid glycosyltransferases, suberin-related 3-ketoacyl-CoA synthase and actin indicated that downregulation of the anthocyanin-specific pathway does not reflect global repression of the wound-periderm transcriptome. Loss of pigmentation may result from reduced expression of the Myb-bHLH-WD40 anthocyanin regulatory complex--a possible candidate might be the bHLH transcription factor JAF13.
Tamura, Satoru; Tsuji, Kouji; Yongzhen, Piao; Ohnishi-Kameyama, Mayumi; Murakami, Nobutoshi
Six new acylated anthocyanins (1-6) were isolated along with the three known congeners (7-9) from the fresh roots of red radishes (Raphanus sativus L.) cultivated by our group. Their chemical structures were elucidated by spectroscopic properties. Among the six new anthocyanins, the five constituents (1, 2, 4-6) were shown to contain the malonyl function at 6-OH in the glucopyranosyl residue linked to C-5 in the pelargonidin nucleus.
Phippen, W B; Simon, J E
The instability of the purple pigments (anthocyanins) in purple basil varieties (Ocimum basilicum L.) limits their use as ornamental plants and as a potential anthocyanin source. Several self-pollinated generations of all purple plants were unsuccessful in stabilizing anthocyanin expression. In this study we investigated the inheritance and stability patterns of leaf traits using the Purple Ruffles variety. The results from the complete diallele crosses indicated anthocyanin expression in vegetative tissue is controlled by two dominant genes and ruffled leaf texture is controlled by a single recessive gene. Genes controlling leaf margin and leaf base structures were tightly linked to leaf texture. Essential oil production and oil constituents in leaves did not change as a result of the reversion in color. Color stability in cuttings was affected by the environment and the location where cuttings were taken. An accumulation of secondary metabolites (apigenin, genistein, and kaempferol) in green-reverted sectors on purple leaves was detected using reverse-phase high-performance liquid chromatography (HPLC) analysis; this suggested a potential block in the anthocyanin pathway. We hypothesize the reversion mutation is occurring in an anthocyanin regulatory gene.
Chanoca, Alexandra; Ueda, Takashi; Grotewold, Erich
Anthocyanins are flavonoid pigments synthesized in the cytoplasm and stored inside vacuoles. Many plant species accumulate densely packed, 3- to 10-μm diameter anthocyanin deposits called anthocyanin vacuolar inclusions (AVIs). Despite their conspicuousness and importance in organ coloration, the origin and nature of AVIs have remained controversial for decades. We analyzed AVI formation in cotyledons of different Arabidopsis thaliana genotypes grown under anthocyanin inductive conditions and in purple petals of lisianthus (Eustoma grandiorum). We found that cytoplasmic anthocyanin aggregates in close contact with the vacuolar surface are directly engulfed by the vacuolar membrane in a process reminiscent of microautophagy. The engulfed anthocyanin aggregates are surrounded by a single membrane derived from the tonoplast and eventually become free in the vacuolar lumen like an autophagic body. Neither endosomal/prevacuolar trafficking nor the autophagy ATG5 protein is involved in the formation of AVIs. In Arabidopsis, formation of AVIs is promoted by both an increase in cyanidin 3-O-glucoside derivatives and by depletion of the glutathione S-transferase TT19. We hypothesize that this novel microautophagy mechanism also mediates the transport of other flavonoid aggregates into the vacuole. PMID:26342015
Monrad, Jeana K; Howard, Luke R; King, Jerry W; Srinivas, Keerthi; Mauromoustakos, Andy
Accelerated solvent extraction (ASE) was used to optimize and determine the effectiveness of an alternative, environmentally friendly extraction procedure using subcritical solvents to recover anthocyanins from freeze-dried, ground Sunbelt red grape pomace. Anthocyanins were extracted from pomace using the following ASE variables: pressure (6.8 MPa), one extraction cycle, and temperature (40, 60, 80, 100, 120, and 140 degrees C). Conventional solvent extraction with methanol/water/formic acid (60:37:3 v/v/v) was compared to four hydroethanolic solvents (10, 30, 50, and 70% ethanol in water, v/v). Anthocyanins in the extracts were identified and quantified by HPLC-MS and HPLC. There was an insignificant interaction between solvent and temperature (p = 0.0663). Solvents containing 70 and 50% ethanol in water extracted more total anthocyanins (463 and 455 mg/100 g of DW, respectively) than other solvents. The total amounts of anthocyanins extracted at 100 degrees C (450 mg/100 g of DW), 80 degrees C (436 mg/100 g of DW), and 120 degrees C (411 mg/100 g of DW) were higher than at the other temperatures. Solvents containing 70 and 50% ethanol in water extracted similar amounts of anthocyanins as conventional extraction solvent.
Yuan, Yao-Wu; Sagawa, Janelle M; Frost, Laura; Vela, James P; Bradshaw, Harvey D
A molecular description of the control of floral pigmentation in a multi-species group displaying various flower color patterns is of great interest for understanding the molecular bases of phenotypic diversification and pollinator-mediated speciation. Through transcriptome profiling, mutant analyses and transgenic experiments, we aim to establish a 'baseline' floral anthocyanin regulation model in Mimulus lewisii and to examine the different ways of tinkering with this model in generating the diversity of floral anthocyanin patterns in other Mimulus species. We find one WD40 and one bHLH gene controlling anthocyanin pigmentation in the entire corolla of M. lewisii and two R2R3-MYB genes, PELAN and NEGAN, controlling anthocyanin production in the petal lobe and nectar guide, respectively. The autoregulation of NEGAN might be a critical property to generate anthocyanin spots. Independent losses of PELAN expression (via different mechanisms) explain two natural yellow-flowered populations of M. cardinalis (typically red-flowered). The NEGAN ortholog is the only anthocyanin-activating MYB expressed in the M. guttatus flowers. The mutant lines and transgenic tools available for M. lewisii will enable gene-by-gene replacement experiments to dissect the genetic and developmental bases of more complex floral color patterns, and to test hypotheses on phenotypic evolution in general. © 2014 The Authors. © 2014 The Authors New Phytologist © 2014 New Phytologist Trust.
Yuan, Yao-Wu; Sagawa, Janelle M.; Frost, Laura; Vela, James P.; Bradshaw, Harvey D.
Summary A molecular description of the control of floral pigmentation in a multi-species group displaying various flower color patterns is of great interest for understanding the molecular bases of phenotypic diversification and pollinator-mediated speciation. Through transcriptome profiling, mutant analyses, and transgenic experiments, we aim to establish a ‘baseline’ floral anthocyanin regulation model in Mimulus lewisii and to examine the different ways of tinkering with this model in generating the diversity of floral anthocyanin patterns in other Mimulus species. We find one WD40 and one bHLH gene controlling anthocyanin pigmentation in the entire corolla of M. lewisii, and two R2R3-MYB genes, PELAN and NEGAN, controlling anthocyanin production in the petal lobe and nectar guide, respectively. The autoregulation of NEGAN might be a critical property to generate anthocyanin spots. Independent losses of PELAN expression (via different mechanisms) explain two natural yellow-flowered populations of M. cardinalis (typically red-flowered). The NEGAN ortholog is the only anthocyanin-activating MYB expressed in the M. guttatus flowers. The mutant lines and transgenic tools available for M. lewisii will enable gene-by-gene replacement experiments to dissect the genetic and developmental bases of more complex floral color patterns, and to test hypotheses on phenotypic evolution in general. PMID:25103615
Aqil, Farrukh; Vadhanam, Manicka V; Jeyabalan, Jeyaprakash; Cai, Jian; Singh, Inder P; Gupta, Ramesh C
Dietary polyphenols may contribute to the prevention of several degenerative diseases, including cancer. Anthocyanins have been shown to possess potential anticancer activity. The aim of this study was to determine anthocyanin bioavailability in lung tissue of mice fed a blueberry diet (5% w/w) for 10 days or a bolus dose (10 mg/mouse; po) of a native mixture of bilberry anthocyanidins. All five anthocyanidins present in the blueberry were detected in the lung tissue using improved methods. The effect of various solvents on the stability of anthocyanins and their recovery from the biomatrix was analyzed. Detection of anthocyanins and their metabolites was performed by UPLC and LC-MS. Although anthocyanins were not detected, cyanidin was detected by UPLC-PDA and other anthocyanidins were detected by LC-MS, following conversion to anthocyanidins and selective extraction in isoamyl alcohol. The results show that anthocyanins can be detected in lung tissue of blueberry-fed mice and thus are bioavailable beyond the gastrointestinal tract.
Bassolino, Laura; Zhang, Yang; Schoonbeek, Henk-Jan; Kiferle, Claudia; Perata, Pierdomenico; Martin, Cathie
Shelf life is one of the most important traits for the tomato (Solanum lycopersicum) industry. Two key factors, post-harvest over-ripening and susceptibility to post-harvest pathogen infection, determine tomato shelf life. Anthocyanins accumulate in the skin of Aft/Aft atv/atv tomatoes, the result of introgressing alleles affecting anthocyanin biosynthesis in fruit from two wild relatives of tomato, which results in extended fruit shelf life. Compared with ordinary, anthocyanin-less tomatoes, the fruits of Aft/Aft atv/atv keep longer during storage and are less susceptible to Botrytis cinerea, a major tomato pathogen, post-harvest. Using genetically modified tomatoes over-producing anthocyanins, we confirmed that skin-specific accumulation of anthocyanins in tomato is sufficient to reduce the susceptibility of fruit to Botrytis cinerea. Our data indicate that accumulation of anthocyanins in tomato fruit, achieved either by traditional breeding or genetic engineering can be an effective way to extend tomato shelf life.
Mazza, G; Cacace, Juan E; Kay, Colin D
Anthocyanins are the largest group of water-soluble pigments in the plant kingdom. They are responsible for most of the red, blue, and purple colors of fruits, vegetables, flowers, and other plant tissues or products. The analysis of anthocyanins is complex as a result of their ability to undergo structural transformations and complexation reactions. In addition, they are difficult to measure independently of other flavonoids, as they have similar structural and reactivity characteristics. Anthocyanins are generally extracted with weakly acidified alcohol-based solvents, followed by concentration (under vacuum), and purification of the pigments. Paper and/or thin-layer chromatography and UV-Vis spectroscopy have traditionally been used for the identification of anthocyanins. Capillary zone electrophoresis, a hybrid of chromatography and electrophoresis, is gaining popularity for the analysis of anthocyanins; however, liquid chromatography (LC) has become the standard method for identification and separation in most laboratories and may be used for both preparative and quantitative analysis. LC with mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy are possibly the most powerful methods for the structural elucidation of anthocyanins available, to date. At present, the most satisfactory method for mixture analysis is the multistep method of separation, isolation, and quantification by LC with peak identification by MS and high-field NMR.
Willemse, Chandré M; Stander, Maria A; Tredoux, Andreas G J; de Villiers, André
Anthocyanins are naturally occurring plant pigments whose accurate analysis is hampered by their complexity and unique chromatographic behaviour associated with on-column conversion reactions. This paper reports the evaluation of off-line comprehensive two-dimensional liquid chromatography (LC×LC) for the analysis of anthocyanins. Hydrophilic interaction chromatography (HILIC) was used in the first dimension in combination with reversed phase liquid chromatography (RP-LC) in the second dimension. For the selective detection of anthocyanins, diode array detection was used, while high resolution quadrupole-time-of-flight mass spectrometry (Q-TOF) was used for compound identification. As application, the HILIC×RP-LC separation of diverse anthocyanins in blueberries, red radish, black beans, red grape skins and red cabbage is demonstrated. Off-line HILIC×RP-LC revealed information which could not be obtained by one-dimensional HPLC methods, while the structured elution order for the anthocyanins simplifies compound identification and facilitates the comparison of anthocyanin content of natural products by means of contour plots.
Flamini, Riccardo; Mattivi, Fulvio; De Rosso, Mirko; Arapitsas, Panagiotis; Bavaresco, Luigi
Grape is qualitatively and quantitatively very rich in polyphenols. In particular, anthocyanins, flavonols and stilbene derivatives play very important roles in plant metabolism, thanks to their peculiar characteristics. Anthocyanins are responsible for the color of red grapes and wines and confer organoleptic characteristics on the wine. They are used for chemotaxonomic studies and to evaluate the polyphenolic ripening stage of grape. They are natural colorants, have antioxidant, antimicrobial and anticarcinogenic activity, exert protective effects on the human cardiovascular system, and are used in the food and pharmaceutical industries. Stilbenes are vine phytoalexins present in grape berries and associated with the beneficial effects of drinking wine. The principal stilbene, resveratrol, is characterized by anticancer, antioxidant, anti-inflammatory and cardioprotective activity. Resveratrol dimers and oligomers also occur in grape, and are synthetized by the vine as active defenses against exogenous attack, or produced by extracellular enzymes released from pathogens in an attempt to eliminate undesirable toxic compounds. Flavonols are a ubiquitous class of flavonoids with photo-protection and copigmentation (together with anthocyanins) functions. The lack of expression of the enzyme flavonoid 3′,5′-hydroxylase in white grapes restricts the presence of these compounds to quercetin, kaempferol and isorhamnetin derivatives, whereas red grapes usually also contain myricetin, laricitrin and syringetin derivatives. In the last ten years, the technological development of analytical instrumentation, particularly mass spectrometry, has led to great improvements and further knowledge of the chemistry of these compounds. In this review, the biosynthesis and biological role of these grape polyphenols are briefly introduced, together with the latest knowledge of their chemistry. PMID:24084717
Šaponjac, Vesna Tumbas; Gironés-Vilaplana, Amadeo; Djilas, Sonja; Mena, Pedro; Cetković, Gordana; Moreno, Diego A; Canadanović-Brunet, Jasna; Vulić, Jelena; Stajčić, Slađana; Krunić, Milica
The global interest in natural food colours shows increasing attention towards new product development to replace synthetic colourants, because of the strengthening of legislative rules and consumer awareness of synthetic additives and chemicals in food. This study was designed to evaluate anthocyanin content and biological activities of press residues from four caneberries: two raspberry (Rubus idaeus, cv. 'Meeker' (RM) and 'Willamette' (RW)) and two blackberry (Rubus fruticosus, cv. 'Thornfree' (BT) and 'Čačanska bestrna' (BC)) cultivars. Analysis by high-performance liquid chromatography-diode array detection-electrospray ionization-tandem mass spectrometry identified cyanidin glycosides in all press residues, cyanidin 3-glucoside being prevalent in BC (1360.6 mg kg(-1)) and BT (1397.7 mg kg(-1)), and cyanidin 3-sophoroside in RM (349.2 mg kg(-1) ) and RW (581.0 mg kg(-1)). Antioxidant capacity (AC), evaluated by ABTS (2,2'-azino-bis(3-ethyl benzothiazoline-6-sulfonic acid) assay, reducing power (RP) and α-glucosidase inhibitory potential (α-GIP) was higher in blackberry press residues. Total anthocyanin content was in good correlation with AC (r = 0.953; P < 0.05), RP (r = 0.993, P < 0.01) and α-GIP (r = 0.852, P < 0.15). This study has revealed the potential for valorization of juice production byproducts for further industrial use as a rich source of bioactive compounds and natural colourants (mainly anthocyanins). Also, they can provide health-promoting effects beyond their general organoleptic acceptance in food product development. © 2014 Society of Chemical Industry.
Flamini, Riccardo; Mattivi, Fulvio; De Rosso, Mirko; Arapitsas, Panagiotis; Bavaresco, Luigi
Grape is qualitatively and quantitatively very rich in polyphenols. In particular, anthocyanins, flavonols and stilbene derivatives play very important roles in plant metabolism, thanks to their peculiar characteristics. Anthocyanins are responsible for the color of red grapes and wines and confer organoleptic characteristics on the wine. They are used for chemotaxonomic studies and to evaluate the polyphenolic ripening stage of grape. They are natural colorants, have antioxidant, antimicrobial and anticarcinogenic activity, exert protective effects on the human cardiovascular system, and are used in the food and pharmaceutical industries. Stilbenes are vine phytoalexins present in grape berries and associated with the beneficial effects of drinking wine. The principal stilbene, resveratrol, is characterized by anticancer, antioxidant, anti-inflammatory and cardioprotective activity. Resveratrol dimers and oligomers also occur in grape, and are synthetized by the vine as active defenses against exogenous attack, or produced by extracellular enzymes released from pathogens in an attempt to eliminate undesirable toxic compounds. Flavonols are a ubiquitous class of flavonoids with photo-protection and copigmentation (together with anthocyanins) functions. The lack of expression of the enzyme flavonoid 3',5'-hydroxylase in white grapes restricts the presence of these compounds to quercetin, kaempferol and isorhamnetin derivatives, whereas red grapes usually also contain myricetin, laricitrin and syringetin derivatives. In the last ten years, the technological development of analytical instrumentation, particularly mass spectrometry, has led to great improvements and further knowledge of the chemistry of these compounds. In this review, the biosynthesis and biological role of these grape polyphenols are briefly introduced, together with the latest knowledge of their chemistry.
Jensen, Morten Busch; López-de-Dicastillo Bergamo, Carolina Ana; Payet, René Marc; Liu, Xueming; Konczak, Izabela
Davidson's plum (Davidsonia pruriens, F. Muell.), a native to Australian rainforests, large, crimson-red fruit, which superficially resembles plum, has been commercially cultivated in Australia since 1990s. The current production volume exceeds market demands therefore this study was designed to evaluate the suitability of Davidson's plum extract as a source of anthocyanin-based food colorant. The stability of the Davidson's plum extract towards heat treatment at 95 °C was higher than that of commercial mulberry colorant, but inferior to colorants derived from red cabbage and purple sweetpotato. An addition of a variety of phenolic acids significantly increased color intensity indicating the formation of copigmentation complexes. Commercial chlorogenic acid as well as extract from a native Australian herb rich in chlorogenic acid, Tasmannia pepper leaf (Tasmannia lanceolata, R. Br.), were both tested in model soft drink solutions subjected to light irradiation and heat treatment. In both cases, the addition of the copigment resulted in a lasting increase in color intensity. In conclusion, Davidson's plum extract can successfully be utilized as a source of natural food color. Extract from Tasmania pepper leaf can be used as a co-pigment for Davidson's plum anthocyanins. The color properties of an anthocyanin colorant derived from the native Australian fruit Davidson's plum are comparable to those of mulberry, which is currently applied as a food colorant in Australian food products. Utilization of Davidson's plum fruit as a source of natural color will allow the industry to increase the range of natural pigments and will create new opportunities for the emerging native food industry.
Jaakola, Laura; Määttä, Kaisu; Pirttilä, Anna Maria; Törrönen, Riitta; Kärenlampi, Sirpa; Hohtola, Anja
The production of anthocyanins in fruit tissues is highly controlled at the developmental level. We have studied the expression of flavonoid biosynthesis genes during the development of bilberry (Vaccinium myrtillus) fruit in relation to the accumulation of anthocyanins, proanthocyanidins, and flavonols in wild berries and in color mutants of bilberry. The cDNA fragments of five genes from the flavonoid pathway, phenylalanine ammonia-lyase, chalcone synthase, flavanone 3-hydroxylase, dihydroflavonol 4-reductase, and anthocyanidin synthase, were isolated from bilberry using the polymerase chain reaction technique, sequenced, and labeled with a digoxigenin-dUTP label. These homologous probes were used for determining the expression of the flavonoid pathway genes in bilberries. The contents of anthocyanins, proanthocyanidins, and flavonols in ripening bilberries were analyzed with high-performance liquid chromatography-diode array detector and were identified using a mass spectrometry interface. Our results demonstrate a correlation between anthocyanin accumulation and expression of the flavonoid pathway genes during the ripening of berries. At the early stages of berry development, procyanidins and quercetin were the major flavonoids, but the levels decreased dramatically during the progress of ripening. During the later stages of ripening, the content of anthocyanins increased strongly and they were the major flavonoids in the ripe berry. The expression of flavonoid pathway genes in the color mutants of bilberry was reduced. A connection between flavonol and anthocyanin synthesis in bilberry was detected in this study and also in previous data collected from flavonol and anthocyanin analyses from other fruits. In accordance with this, models for the connection between flavonol and anthocyanin syntheses in fruit tissues are presented.
Jaakola, Laura; Määttä, Kaisu; Pirttilä, Anna Maria; Törrönen, Riitta; Kärenlampi, Sirpa; Hohtola, Anja
The production of anthocyanins in fruit tissues is highly controlled at the developmental level. We have studied the expression of flavonoid biosynthesis genes during the development of bilberry (Vaccinium myrtillus) fruit in relation to the accumulation of anthocyanins, proanthocyanidins, and flavonols in wild berries and in color mutants of bilberry. The cDNA fragments of five genes from the flavonoid pathway, phenylalanine ammonia-lyase, chalcone synthase, flavanone 3-hydroxylase, dihydroflavonol 4-reductase, and anthocyanidin synthase, were isolated from bilberry using the polymerase chain reaction technique, sequenced, and labeled with a digoxigenin-dUTP label. These homologous probes were used for determining the expression of the flavonoid pathway genes in bilberries. The contents of anthocyanins, proanthocyanidins, and flavonols in ripening bilberries were analyzed with high-performance liquid chromatography-diode array detector and were identified using a mass spectrometry interface. Our results demonstrate a correlation between anthocyanin accumulation and expression of the flavonoid pathway genes during the ripening of berries. At the early stages of berry development, procyanidins and quercetin were the major flavonoids, but the levels decreased dramatically during the progress of ripening. During the later stages of ripening, the content of anthocyanins increased strongly and they were the major flavonoids in the ripe berry. The expression of flavonoid pathway genes in the color mutants of bilberry was reduced. A connection between flavonol and anthocyanin synthesis in bilberry was detected in this study and also in previous data collected from flavonol and anthocyanin analyses from other fruits. In accordance with this, models for the connection between flavonol and anthocyanin syntheses in fruit tissues are presented. PMID:12376640
Kilmister, Rachel L; Mazza, Marica; Baker, Nardia K; Faulkner, Peta; Downey, Mark O
Four wines were made to investigate the effect of different anthocyanin and tannin fruit concentrations on wine phenolics and colour. Wines that were made from fruit with high anthocyanin concentration had high tannin concentrations regardless of the concentration of tannin in fruit, while wines made from fruit with low anthocyanin also had low tannin concentration. It was found that fruit anthocyanin concentration correlated with wine tannin concentration, wine colour and polymeric pigment formation. Anthocyanin concentration might be a key component for increasing tannin solubility and extraction into wine and the formation of polymeric pigments. Industry implications include managing tannin and anthocyanin fruit concentration for targeting tannin extraction and polymeric pigment formation in wine.
Li, Jian-Bin; Hashimoto, Fumio; Shimizu, Keiichi; Sakata, Yusuke
Twelve anthocyanins (1-12) were isolated from the red flowers of Camellia hongkongensis Seem. by chromatography using open columns. Their structures were elucidated on the basis of spectroscopic analyses, that is, proton-nuclear magnetic resonance, carbon 13-nuclear magnetic resonance, heteronuclear multiple quantum correlation, heteronuclear multiple bond correlation, high resolution electrospray ionization mass and ultraviolet visible spectroscopies. Out of these anthocyanins, a novel acylated anthocyanin, cyanidin 3-O-(6-O-(Z)-p-coumaroyl)-beta-galactopyranoside (6), two known acylated anthocyanins, cyanidin 3-O-(6-O-(E)-p-coumaroyl)-beta-galactopyranoside (7) and cyanidin 3-O-(6-O-(E)-caffeoyl)-beta-galactopyranoside (8), and three known delphinidin glycosides (10-12) were for the first time isolated from the genus Camellia. Furthermore, pigment components in C. japonica L., C. chekiangoleosa Hu and C. semiserrata Chi were studied. The results indicated that the distribution of anthocyanins was differed among these species. Delphinidin glycoside was only detected in the flowers of C. hongkongensis, which is a special and important species in the section Camellia. Based on the characterization of anthocyanins in the section Camellia species, there is a close relationship among these species, and C. hongkongensis might be an important parent for creating new cultivars with bluish flower color.
Hlavinka, Jan; Nauš, Jan; Špundová, Martina
Leaf chlorophyll content is an important physiological parameter which can serve as an indicator of nutritional status, plant stress or senescence. Signals proportional to the chlorophyll content can be measured non-destructively with instruments detecting leaf transmittance (e.g., SPAD-502) or reflectance (e.g., showing normalized differential vegetation index, NDVI) in red and near infrared spectral regions. The measurements are based on the assumption that only chlorophylls absorb in the examined red regions. However, there is a question whether accumulation of other pigments (e.g., anthocyanins) could in some cases affect the chlorophyll meter readings. To answer this question, we cultivated tomato plants (Solanum lycopersicum L.) for a long time under low light conditions and then exposed them for several weeks (4 h a day) to high sunlight containing the UV-A spectral region. The senescent leaves of these plants evolved a high relative content of anthocyanins and visually revealed a distinct blue color. The SPAD and NDVI data were collected and the spectra of diffusive transmittance and reflectance of the leaves were measured using an integration sphere. The content of anthocyanins and chlorophylls was measured analytically. Our results show that SPAD and NDVI measurement can be significantly affected by the accumulated anthocyanins in the leaves with relatively high anthocyanin content. To describe theoretically this effect of anthocyanins, concepts of a specific absorbance and a leaf spectral polarity were developed. Corrective procedures of the chlorophyll meter readings for the anthocyanin contribution are suggested both for the transmittance and reflectance mode.
Di Fabio, Amanda; Salomón, Susana; Lanfranchi, Héctor
Background: Oxidative stress is involved in oral lichen planus (OLP) pathogenesis; meanwhile anthocyanins are natural antioxidants present in grapes skin. Objectives: The aim of this research was to verify the utility of anthocyanins, extracted from grapes skin, for the local treatment of oral lichen planus and to compare it with clobetasol propionate- neomycin -nystatin cream (CP-NN). Study Design: Prospective, non-randomized study, with control group. Fifty-two patients with OLP were included. We divided patients into two categories: erosive oral lichen planus (EOLP) and non erosive oral lichen planus (NEOLP). 38 had EOLP (17 cases and 21 controls) and 14 presented NEOLP types (9 cases and 5 controls).Cases received local treatment with anthocyanins from grapes and controls, were treated with CP-NN. The clinical evolution of patients was followed up during six months. Results: The patients had a therapeutic response with anthocyanins. This was better than CP-NN treatment for patients with EOLP, in improving the involvement score of the oral mucosa and in the morphometric study of the affected areas. In EOLP there were no statistically significant differences in: therapeutic response time, the evolution of pain, or the relapse rate between the two groups. With respect to the treatment of NEOLP there was improved pain relief in the group treated with anthocyanins. This was not observed with CP-NN. The resting analized variables showed no significant difference with both treatments. Conclusions: OLP has a favorable response to local treatment with anthocyanins from grapes. We found an equal to or better response than with CP-NN treatment. Many of our patients have systemic diseases, which may contraindicate the use of steroids. With regard to this particular group, the use of this natural antioxidant present in the diet is considered advantageous. Key words:Anthocyanins, antioxidants, chemoprevention, morphometry, oral lichen, oxidative stress. PMID:24880442
Zhou, Zhou; Nair, Muraleedharan G; Claycombe, Kate J
Studies have shown positive correlations between inflammatory cytokines such as interleukin-6 (IL-6) and the development of chronic diseases including cardiovascular disease by activating C-reactive protein (CRP). Both atorvastatin calcium (lipitor) as well as flavonoid rich fruit such as tart cherry demonstrate potent anti-inflammatory effects on IL-6 secretion. In this study, we investigated whether tart cherry extract or specific anthocyanins contained in the tart cherry show synergistic anti-inflammatory effects with lipitor. Results showed that LPS-induced adipose stem cell secretion of IL-6 reduced with the addition of tart cherry extract, a mixture of tart cherry anthocyanins, and pure tart cherry cyanidin-3-O-glucoside (C3G) in a dose-dependent manner. Furthermore, lipitor and C3G exhibited synergistic effects in reducing LPS-induced IL-6 secretion from adipose stem cells. In conclusion, these results support potential benefits of using dietary phytochemicals in conjunction with pharmacological therapies to decrease adipose inflammation, drug doses, and ultimately, drug-induced adverse effects.
Rojo, Leonel E; Ribnicky, David; Logendra, Sithes; Poulev, Alex; Rojas-Silva, Patricio; Kuhn, Peter; Dorn, Ruth; Grace, Mary H.; Lila, Mary Ann; Raskin, Ilya
We used a murine model of type II diabetes, which reproduces the major features of the human disease, and a number of cellular models to study the antidiabetic effect of ANC, a standardised anthocyanin-rich formulation from maqui berry (Aristotelia chilensis). We also isolated delphinidin 3-sambubioside-5-glucoside (D3S5G), a characteristic anthocyanin from maqui berry, and studied its antidiabetic properties. We observed that oral administration of ANC improved fasting blood glucose levels and glucose tolerance in hyperglycaemic obese C57BL/6J mice fed a high fat diet. In H4IIE rat liver cells, ANC decreased glucose production and enhanced the insulin-stimulated down regulation of the gluconeogenic enzyme, glucose-6-phosphatase. In L6 myotubes ANC treatment increased both insulin and non-insulin mediated glucose uptake. As with the ACN, oral administration of pure D3S5G dose-dependently decreased fasting blood glucose levels in obese C57BL/6J mice, and decreased glucose production in rat liver cells. D3S5G also increased glucose uptake in L6 myotubes and is at least partially responsible for ANC’s anti-diabetic properties. PMID:26279603
Liu, Yixiang; Zhang, Di; Wu, Yongpei; Wang, Dan; Wei, Ying; Wu, Jiulin; Ji, Baoping
Numerous studies have shown that anthocyanins usually have better in vitro bioactivity than in vivo bioactivity. This may be due to physiochemical degradation during gastrointestinal digestion and their poor bioavailability in in vivo studies. Therefore, this study aims to investigate the effects of anthocyanin structure on their stability under simulated gastrointestinal digestion and to assess their absorption in the intestines using Caco-2 human intestinal cell monolayers. The results show that gastric digestion does not significant affect blueberry anthocyanins in terms of composition and antioxidative activity. However, approximately 42% of the total anthocyanin and 29% of the antioxidative activity were lost during intestinal digestion. Structural analysis indicated that fewer free hydroxyl groups and more methoxy groups in the B-ring improve anthocyanin stability. The absorption trials demonstrated that more hydrophobic anthocyanins have better absorption efficiency than more hydrophilic anthocyanins. Furthermore, the glycoside structure also determines the absorption efficiency of anthocyanins.
Bennett, Michael D.; Price, H. James; Johnston, J. Spencer
Background Measuring genome size by flow cytometry assumes direct proportionality between nuclear DNA staining and DNA amount. By 1997 it was recognized that secondary metabolites may affect DNA staining, thereby causing inaccuracy. Here experiments are reported with poinsettia (Euphorbia pulcherrima) with green leaves and red bracts rich in phenolics. Methods DNA content was estimated as fluorescence of propidium iodide (PI)-stained nuclei of poinsettia and/or pea (Pisum sativum) using flow cytometry. Tissue was chopped, or two tissues co-chopped, in Galbraith buffer alone or with six concentrations of cyanidin-3-rutinoside (a cyanidin-3-rhamnoglucoside contributing to red coloration in poinsettia). Key Results There were large differences in PI staining (35–70 %) between 2C nuclei from green leaf and red bract tissue in poinsettia. These largely disappeared when pea leaflets were co-chopped with poinsettia tissue as an internal standard. However, smaller (2·8–6·9 %) differences remained, and red bracts gave significantly lower 1C genome size estimates (1·69–1·76 pg) than green leaves (1·81 pg). Chopping pea or poinsettia tissue in buffer with 0–200 µm cyanidin-3-rutinoside showed that the effects of natural inhibitors in red bracts of poinsettia on PI staining were largely reproduced in a dose-dependent way by this anthocyanin. Conclusions Given their near-ubiquitous distribution, many suspected roles and known affects on DNA staining, anthocyanins are a potent, potential cause of significant error variation in genome size estimations for many plant tissues and taxa. This has important implications of wide practical and theoretical significance. When choosing genome size calibration standards it seems prudent to select materials producing little or no anthocyanin. Reviewing the literature identifies clear examples in which claims of intraspecific variation in genome size are probably artefacts caused by natural variation in anthocyanin levels or
Mancinelli, A L; Walsh, L
Light-dependent anthocyanin synthesis is a typical high irradiance response (HIR) of plant photomorphogenesis. The spectral sensitivity of this response in young seedlings of cabbage and tomato is strongly affected by the length and mode of application of the light treatments. This observation suggests that the different experimental conditions, used in different action spectroscopy studies, might have been responsible, at least in part, for some of the reported differences in the characteristics of the HIR action spectra of different response-system combinations. In both cabbage and tomato, the values of the far red/blue, far red/red, and blue/red action ratios increase with increasing durations of the light treatments; this finding is in agreement with hypotheses of K. M. Hartmann (1966, 1967) and E. Schäfer (1975) for phytochrome action in the HIR. The similarity in the trend of change of the values of the action ratios suggests the possibility that the photomorphogenic pigment system, involved in the photoregulation of anthocyanin synthesis, may be the same in cabbage and tomato, even though there are some differences in the spectral sensitivity of the response between the two species.
Provenzano, Sofia; Spelt, Cornelis; Hosokawa, Satoko; Nakamura, Noriko; Brugliera, Filippa; Demelis, Linda; Geerke, Daan P.; Schubert, Andrea; Tanaka, Yoshikazu; Quattrocchio, Francesca; Koes, Ronald
Anthocyanins are a chemically diverse class of secondary metabolites that color most flowers and fruits. They consist of three aromatic rings that can be substituted with hydroxyl, sugar, acyl, and methyl groups in a variety of patterns depending on the plant species. To understand how such chemical diversity evolved, we isolated and characterized METHYLATION AT THREE2 (MT2) and the two METHYLATION AT FIVE (MF) loci from Petunia spp., which direct anthocyanin methylation in petals. The proteins encoded by MT2 and the duplicated MF1 and MF2 genes and a putative grape (Vitis vinifera) homolog Anthocyanin O-Methyltransferase1 (VvAOMT1) are highly similar to and apparently evolved from caffeoyl-Coenzyme A O-methyltransferases by relatively small alterations in the active site. Transgenic experiments showed that the Petunia spp. and grape enzymes have remarkably different substrate specificities, which explains part of the structural anthocyanin diversity in both species. Most strikingly, VvAOMT1 expression resulted in the accumulation of novel anthocyanins that are normally not found in Petunia spp., revealing how alterations in the last reaction can reshuffle the pathway and affect (normally) preceding decoration steps in an unanticipated way. Our data show how variations in gene expression patterns, loss-of-function mutations, and alterations in substrate specificities all contributed to the anthocyanins’ structural diversity. PMID:24830298
Thamaphat, Kheamrutai; Goodman, Bernard A; Limsuwan, Pichet; Smith, Siwaporn Meejoo
Anthocyanin, which is soluble in water and released into sugar steam during extraction, was investigated in this study. The anthocyanin content in refined sugar, plantation white sugar, soft brown sugar and raw sugar was determined using electron spin resonance (ESR) spectroscopy, which was operated at room temperature, and compared with spectra from standard anthocyanin. The ESR spectra of red and violet anthocyanins was predominantly g ≈ 2.0055, which corresponded to an unpaired electron located in the pyrylium ring. Signals for Fe(III) and Mn(II), which naturally occur in plants, were found in raw sugar, soft brown sugar and standard anthocyanin but were absent from refined sugar and plantation white sugar due to the refining process. In addition, the ESR results were correlated with the apparent colour of the sugar, which was determined using the method of the International Commission for Uniform Methods of Sugar Analysis and inductively coupled plasma optical emission spectroscopy. Copyright © 2014 Elsevier Ltd. All rights reserved.
Garcia-Lor, Andrés; Licciardello, Concetta; Las Casas, Giuseppina; Ramadugu, Chandrika; Krueger, Robert; Fanciullino, Anne-Laure; Froelicher, Yann
Mandarin (Citrus reticulata), citron (Citrus medica), and pummelo (Citrus maxima) are important species of the genus Citrus and parents of the interspecific hybrids that constitute the most familiar commercial varieties of Citrus: sweet orange, sour orange, clementine, lemon, lime, and grapefruit. Citron produces anthocyanins in its young leaves and flowers, as do species in genera closely related to Citrus, but mandarins do not, and pummelo varieties that produce anthocyanins have not been reported. We investigated the activity of the Ruby gene, which encodes a MYB transcription factor controlling anthocyanin biosynthesis, in different accessions of a range of Citrus species and in domesticated cultivars. A white mutant of lemon lacks functional alleles of Ruby, demonstrating that Ruby plays an essential role in anthocyanin production in Citrus. Almost all the natural variation in pigmentation by anthocyanins in Citrus species can be explained by differences in activity of the Ruby gene, caused by point mutations and deletions and insertions of transposable elements. Comparison of the allelic constitution of Ruby in different species and cultivars also helps to clarify many of the taxonomic relationships in different species of Citrus, confirms the derivation of commercial varieties during domestication, elucidates the relationships within the subgenus Papeda, and allows a new genetic classification of mandarins. PMID:28196843
Khoo, Hock Eng; Azlan, Azrina; Nurulhuda, M. Halid; Ismail, Amin; Abas, Faridah; Hamid, Muhajir; Roowi, Suri
This study aimed to determine anthocyanins and their antioxidative and cardioprotective properties in defatted dabai parts. Anthocyanins in crude extracts and extract fractions of defatted dabai peel and pericarp were quantified using UHPLC, while their antioxidant capacity and oxidative stress inhibition ability were evaluated by using DPPH and CUPRAC assays as well as linoleic acid oxidation system, hemoglobin oxidation, and PARP-1 inhibition ELISA. Cardioprotective effect of the defatted dabai peel extract was evaluated using hypercholesterolemic-induced New Zealand white rabbits. Six anthocyanins were detected in the defatted dabai peel, with the highest antioxidant capacities and oxidative stress inhibition effect compared to the other part. The defatted dabai peel extract has also inhibited lipid peroxidation (plasma MDA) and elevated cellular antioxidant enzymes (SOD and GPx) in the tested animal model. Major anthocyanin (cyanidin-3-glucoside) and other anthocyanins (pelargonidin-3-glucoside, malvidin-3-glucoside, cyanidin-3-galactoside, cyanidin-3-arabinoside, and peonidin-3-glucoside) detected in the defatted dabai peel are potential future nutraceuticals with promising medicinal properties. PMID:24368926
Gouvêa, Ana Cristina M S; Melo, Armindo; Santiago, Manuela C P A; Peixoto, Fernanda M; Freitas, Vitor; Godoy, Ronoel L O; Ferreira, Isabel M P L V O
Neomitranthes obscura (DC.) N. Silveira is a Brazilian fruit belonging to the Myrtaceae family that contains anthocyanins in the peel and was studied for the first time in this work. Delphinidin-3-O-galactoside, delphinidin-3-O-glucoside, cyanidin-3-O-galactoside, cyanidin-3-O-glucoside, cyanidin-3-O-arabinoside, petunidin-3-O-glucoside, pelargonidin-3-O-glucoside, peonidin-3-O-galactoside, peonidin-3-O-glucoside, cyanidin-3-O-xyloside were separated and identified by LC/DAD/MS and by co-elution with standards. Reliable quantification of anthocyanins in the mature fruits was performed by HPLC/DAD using weighted linear regression model from 0.05 to 50mg of cyaniding-3-O-glucoside L(-1) because it gave better fit quality than least squares linear regression. Good precision and accuracy were obtained. The total anthocyanin content of mature fruits was 263.6 ± 8.2 mg of cyanidin-3-O-glucoside equivalents 100 g(-1) fresh weight, which was in the same range found in literature for anthocyanin rich fruits.
Zakhrabekova, Shakhira; Dockter, Christoph; Ahmann, Katharina; Braumann, Ilka; Gough, Simon P; Wendt, Toni; Lundqvist, Udda; Mascher, Martin; Stein, Nils; Hansson, Mats
The erectoides-m anthocyanin-less 1 (ert-m ant1) double mutants are among the very few examples of induced double mutants in barley. From phenotypic observations of mutant plants it is known that the Ert-m gene product regulates plant architecture whereas the Ant1 gene product is involved in anthocyanin biosynthesis. We used a near-isogenic line of the cultivar Bowman, BW316 (ert-m.34), to create four F2-mapping populations by crosses to the barley cultivars Barke, Morex, Bowman and Quench. We phenotyped and genotyped 460 plants, allowing the ert-m mutation to be mapped to an interval of 4.7 cM on the short arm of barley chromosome 7H. Bioinformatic searches identified 21 candidate gene models in the mapped region. One gene was orthologous to a regulator of Arabidopsis thaliana plant architecture, ERECTA, encoding a leucine-rich repeat receptor-like kinase. Sequencing of HvERECTA in barley ert-m mutant accessions identified severe DNA changes in 15 mutants, including full gene deletions in ert-m.40 and ert-m.64. Both deletions, additionally causing anthocyanin deficiency, were found to stretch over a large region including two putative candidate genes for the anthocyanin biosynthesis locus Ant1. Analyses of ert-m and ant1 single- and double-deletion mutants suggest Ant1 as a closely linked gene encoding a R2R3 myeloblastosis transcription factor.
Dixon, Richard A; Liu, Chenggang; Jun, Ji Hyung
Monomeric anthocyanins and polymeric proanthocyanidins (condensed tannins) contribute to important plant traits such as flower and fruit pigmentation, fruit astringency, disease resistance and forage quality. Recent advances in our understanding of the transcriptional control mechanisms that regulate anthocyanin and condensed tannin formation in plants suggest new approaches for the engineering of quality traits associated with these molecules. In particular, MYB family transcription factors are emerging as central players in the coordinated activation of sets of genes specific for the anthocyanin and tannin pathways. Mutations in these genes underlie potentially valuable crop traits, and ectopic over- or under-expression of MYB transcription factors provides routes for engineering of these complex pathways. Copyright © 2012 Elsevier Ltd. All rights reserved.
Nemś, Agnieszka; Pęksa, Anna; Kucharska, Alicja Z; Sokół-Łętowska, Anna; Kita, Agnieszka; Drożdż, Wioletta; Hamouz, Karel
Coloured-fleshed potatoes of four varieties were used as raw material for coloured flour and fried snack production. The effects of thermal processes traditionally used in dried potato processing and in snack pellet manufacturing on anthocyanin profiles, total polyphenols and antioxidant properties of obtained half- and ready products were studied. There was a significant influence of potato variety on the experimental flour and snack properties. Flours with the highest antioxidant activities were obtained from Salad Blue and Herbie 26 potatoes; however, the flour prepared from the Blue Congo exhibited a much higher total polyphenol and anthocyanin content. Snacks produced with coloured flour had 2-3 times higher antioxidant activities, 40% higher contents of polyphenols, attractive colour and better expansion compared to control samples. The lowest losses of anthocyanins during snack processing were in snacks with flour from the purple-fleshed Blue Congo and red-fleshed Herbie 26.
Gottier, Claudia; Biedermann, Luc; Zeitz, Jonas; Lang, Silvia; Weber, Achim; Rogler, Gerhard; Scharl, Michael
Background/Aims We previously demonstrated that anthocyanin-rich bilberry extract (ARBE) inhibits IFN-γ-induced signalling and downstream effects in human monocytic cells and ameliorates disease activity in ulcerative colitis (UC) patients. Here, we studied the molecular mechanisms of ARBE-mediated effects in vitro and by analysing colonic tissue and serum samples of UC patients treated with an oral anthocyanin-rich bilberry preparation during an open label clinical trial. Methods Colon specimens obtained during an open pilot study using ARBE for the treatment of mild-to-moderate UC were analyzed by immunohistochemistry. Cytokine levels in patients’ serum were quantified by ELISA. Cell culture experiments were performed using THP-1 monocytic cells. Results ARBE treatment inhibited the expression of IFN-γ-receptor 2 in human THP-1 monocytic cells. Colon biopsies of UC patients who responded to the 6-week long ARBE treatment revealed reduced amounts of the pro-inflammatory cytokines IFN-γ and TNF-α. Levels of phosphorylated (activated) p65-NF-κB were reduced in these patients. Further, patients with successful ARBE treatment featured enhanced levels of Th17-cell specific cytokine IL-22 and immunoregulatory cytokine IL-10 as well as reduced serum levels of TNF-α and MCP-1, but enhanced levels of IL-17A, in contrast to patients that did not reach remission after ARBE treatment. Conclusions Our data suggest a molecular mechanism underlying the anti-inflammatory effects of ARBE treatment in UC patients by modulating T-cell cytokine signalling and inhibiting IFN-γ signal transduction. These data are of particular interest, since ARBE is a promising therapeutic approach for the treatment of IBD. PMID:27152519
Li, Xiao-Jing; Huang, Xu-Ming; Wang, Hui-Cong
Litchi has diverse fruit color phenotypes, yet no research reflects the biochemical background of this diversity. In this study, we evaluated 12 litchi cultivars for chromatic parameters and pigments, and investigated the effects of abscisic acid, forchlorofenron (CPPU), bagging and debagging treatments on fruit coloration in cv. Feizixiao, an unevenly red cultivar. Six genes encoding chalcone synthase (CHS), chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS) and UDP-glucose: flavonoid 3-O-glucosyltransferase (UFGT) were isolated from the pericarp of the fully red litchi cv. Nuomici, and their expression was analyzed in different cultivars and under the above mentioned treatments. Pericarp anthocyanin concentration varied from none to 734 mg m−2 among the 12 litchi cultivars, which were divided into three coloration types, i.e. non-red (‘Kuixingqingpitian’, ‘Xingqiumili’, ‘Yamulong’and ‘Yongxing No. 2′), unevenly red (‘Feizixiao’ and ‘Sanyuehong’) and fully red (‘Meiguili’, ‘Baila’, Baitangying’ ’Guiwei’, ‘Nuomici’ and ‘Guinuo’). The fully red type cultivars had different levels of anthocyanin but with the same composition. The expression of the six genes, especially LcF3H, LcDFR, LcANS and LcUFGT, in the pericarp of non-red cultivars was much weaker as compared to those red cultivars. Their expression, LcDFR and LcUFGT in particular, was positively correlated with anthocyanin concentrations in the pericarp. These results suggest the late genes in the anthocyanin biosynthetic pathway were coordinately expressed during red coloration of litchi fruits. Low expression of these genes resulted in absence or extremely low anthocyanin accumulation in non-red cultivars. Zero-red pericarp from either immature or CPPU treated fruits appeared to be lacking in anthocyanins due to the absence of UFGT expression. Among these six genes, only the expression of UFGT
Wei, Yong-Zan; Hu, Fu-Chu; Hu, Gui-Bing; Li, Xiao-Jing; Huang, Xu-Ming; Wang, Hui-Cong
Litchi has diverse fruit color phenotypes, yet no research reflects the biochemical background of this diversity. In this study, we evaluated 12 litchi cultivars for chromatic parameters and pigments, and investigated the effects of abscisic acid, forchlorofenron (CPPU), bagging and debagging treatments on fruit coloration in cv. Feizixiao, an unevenly red cultivar. Six genes encoding chalcone synthase (CHS), chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS) and UDP-glucose: flavonoid 3-O-glucosyltransferase (UFGT) were isolated from the pericarp of the fully red litchi cv. Nuomici, and their expression was analyzed in different cultivars and under the above mentioned treatments. Pericarp anthocyanin concentration varied from none to 734 mg m(-2) among the 12 litchi cultivars, which were divided into three coloration types, i.e. non-red ('Kuixingqingpitian', 'Xingqiumili', 'Yamulong'and 'Yongxing No. 2'), unevenly red ('Feizixiao' and 'Sanyuehong') and fully red ('Meiguili', 'Baila', Baitangying' 'Guiwei', 'Nuomici' and 'Guinuo'). The fully red type cultivars had different levels of anthocyanin but with the same composition. The expression of the six genes, especially LcF3H, LcDFR, LcANS and LcUFGT, in the pericarp of non-red cultivars was much weaker as compared to those red cultivars. Their expression, LcDFR and LcUFGT in particular, was positively correlated with anthocyanin concentrations in the pericarp. These results suggest the late genes in the anthocyanin biosynthetic pathway were coordinately expressed during red coloration of litchi fruits. Low expression of these genes resulted in absence or extremely low anthocyanin accumulation in non-red cultivars. Zero-red pericarp from either immature or CPPU treated fruits appeared to be lacking in anthocyanins due to the absence of UFGT expression. Among these six genes, only the expression of UFGT was found significantly correlated with the
Cortell, Jessica M; Halbleib, Michael; Gallagher, Andrew V; Righetti, Timothy L; Kennedy, James A
The relationships between grapevine (Vitis vinifera) vigor variation and resulting wine anthocyanin concentration and composition and pigmented polymer formation were investigated. The study was conducted in a commercial vineyard consisting of the same clone, rootstock, age, and vineyard management practices. Vine vigor parameters were used to designate vigor zones within two vineyard sites (A and B) to produce research wines (2003 and 2004) and conduct a model extraction experiment (2004 only) to investigate the vine-fruit-wine continuum. Wines and model extracts were analyzed by HPLC and UV-vis spectrophotometry. For the model extractions, there were no differences between sites for pomace weight, whereas juice volume was higher for site A. This was not related to a larger berry size. Site A had a higher anthocyanin concentration (milligrams per liter) in the model extracts than site B specifically for the medium- and low-vigor zones. For anthocyanin composition in the model extraction, site B had a greater proportion of malvidin-3-O-glucoside and less of the remaining anthocyanin glucosides (delphinidin, cyanidin, petunidin, and peonidin) compared to site A. In the wines, there was a vintage effect, with the 2003 wines having a higher anthocyanin concentration (milligrams per liter) than the 2004 wines. This appears to have been primarily due to a greater accumulation of anthocyanins in the fruit. In general, the medium-vigor zone wines had higher anthocyanin concentrations than either the high- or low-vigor zone wines. There was also vintage variation related to anthocyanin composition, with the 2003 wines having a higher proportion of delphinidin and petunidin glucosides and lower malvidin-3-O-glucoside compared to 2004. In both years, there were higher proportions of delphinidin and petunidin glucosides in wines made from low-vigor-zone fruit. Wines made from low-vigor zones showed a greater propensity to form vitisin A as well as pigmented polymers. Low
Wang, Yuehua; Zhu, Jinyan; Meng, Xianjun; Liu, Suwen; Mu, Jingjing; Ning, Chong
Four varieties of Lonicera caerulea berries--'Wild', 'Beilei', 'No. 1', and 'No. 2'--were compared with respect to extraction yield, fruit weight, total soluble solids, polyphenol and anthocyanin contents, oxygen radical absorbance capacity (ORAC), and anthocyanin composition. Sixteen individual anthocyanins were identified in the selected varieties. Acylated anthocyanins, cyanidin 3-acetylhexoside and peonidin 3-acetylhexoside, were identified in L. caerulea berries for the first time. Cyanidin-3-glucoside was the most prominent anthocyanin in all four tested varieties. Wild type of L. caerulea fruit ('Wild'), with the highest polyphenol content, contained 14 anthocyanins and the highest ORAC value. Eleven anthocyanins were found in 'Beilei' berries, which had a higher ORAC value than 'No. 1' and 'No. 2'. The highest total soluble solid content and extraction yield were found in 'No. 2' and 'Wild' berries, respectively.
Chokeberries are a rich source of anthocyanins, which may contribute to the prevention of obesity and metabolic syndrome. The aim of this study was to determine if an extract from chokeberries would reduce weight gain in rats fed a fructose-rich diet, and to explore the potential mechanisms related...
Mehta, Amar J; Cassidy, Aedín; Litonjua, Augusto A; Sparrow, David; Vokonas, Pantel; Schwartz, Joel
Background: It is unknown whether habitual intake of dietary flavonoids, known for their antioxidative and anti-inflammatory properties, affects longitudinal change in lung function. Objective: We investigated whether different flavonoid subclasses present in the habitual diet were associated with beneficial changes in lung function over time in the elderly. Design: This longitudinal analysis included 839 participants from the VA (Veterans Affairs) Normative Aging Study whose lung function [forced expiratory volume in 1 s (FEV1) and forced vital capacity (FVC)] was measured at 2 and up to 5 visits between 1992 and 2008 (n = 2623 measurements). Yearly average intake of major flavonoid subclasses (anthocyanins, flavanones, flavan-3-ols, flavonols, flavones, and polymers) was calculated from food-frequency questionnaires at each visit. We estimated adjusted differences in annual change in lung function associated with each flavonoid subclass, categorized into quartiles, in linear mixed-effects regression models after adjustment for lifestyle and dietary confounders. Results: Strong inverse associations were found between anthocyanin intake and age-related decline in lung function. Independent of dietary and nondietary risk factors, slower rates of FEV1 and FVC decline by 23.6 (95% CI: 16.6, 30.7) and 37.3 (95% CI: 27.8, 46.8) mL/y, respectively, were observed in participants in the fourth quartile of intake compared with participants in the first quartile (P-trend < 0.0001). The protective associations observed for anthocyanin intake were present in both current/former and never smokers. Compared with no or very low intakes, an intake of ≥2 servings of anthocyanin-rich blueberries/wk was associated with slower decline in FEV1 and FVC by 22.5 (95% CI: 10.8, 34.2) and 37.9 (95% CI: 22.1, 53.7) mL/y, respectively. To a lesser extent, higher flavan-3-ol intake was also associated with slower lung function decline. Conclusions: An attenuation of age-related lung function
A clinical study was conducted to investigate the dose response and metabolism of strawberry anthocyanins. In a crossover study design, twelve healthy adults consumed each of three strawberry treatments. The treatments were 100 g, 200 g, and 400 g of pureed strawberries, delivering 15 micromol, 30 m...
Overall, John; Bonney, Sierra A.; Wilson, Mickey; Beermann, Arnold; Grace, Mary H.; Esposito, Debora; Lila, Mary Ann; Komarnytsky, Slavko
Overconsumption of energy dense foods and sedentary lifestyle are considered as major causes of obesity-associated insulin resistance and abnormal glucose metabolism. Results from both cohort studies and randomized trials suggested that anthocyanins from berries may lower metabolic risks, however these reports are equivocal. The present study was designed to examine effects of six berries with structurally diverse anthocyanin profiles (normalized to 400 µg/g total anthocyanin content) on development of metabolic risk factors in the C57BL/6 mouse model of polygenic obesity. Diets supplemented with blackberry (mono-glycosylated cyanidins), black raspberry (acylated mono-glycosylated cyanidins), blackcurrant (mono- and di-glycosylated cyanidins and delphinidins), maqui berry (di-glycosylated delphinidins), Concord grape (acylated mono-glycosylated delphinidins and petunidins), and blueberry (mono-glycosylated delphinidins, malvidins, and petunidins) showed a prominent discrepancy between biological activities of delphinidin/malvidin-versus cyanidin-type anthocyanins that could be explained by differences in their structure and metabolism in the gut. Consumption of berries also resulted in a strong shift in the gastrointestinal bacterial communities towards obligate anaerobes that correlated with decrease in the gastrointestinal luminal oxygen and oxidative stress. Further work is needed to understand mechanisms that lead to nearly anoxic conditions in the gut lumens, including the relative contributions of host, diet and/or microbial oxidative activity, and their implication to human health. PMID:28212306
Terahara, N; Honda, T; Hayashi, M; Ishimaru, K
Two new anthocyanins were isolated from purple pods of pea (Pisum spp.). Their structures were identified as delphinidin 3-xylosylgalactoside-5-acetylglucoside and its deacetylated derivative by the usual chemical degradation methods and by spectroscopic methods such as UV-VIS, MS and NMR. Both pigments showed moderate stability and antioxidative activity in a neutral aqueous solution.
Dupeyrón, Danay; Kawakami, Monique; Rieumont, Jacques; Carvalho, José Carlos
Açaí berry, from the Euterpe oleracea Mart. Palm, has been described as the most important fruit in the Brazilian Amazon. Several studies have reported that anthocyanins (ACNs), one of the components of the açaí, have enormous potential for pharmaceuticals applications. However, the bioavailability of anthocyanins is relatively low compared to that of other flavonoids. Then, in the present work, anthocyanins-loaded nanoparticles have been developed to overcome their poor bioavailability. A two-level factorial design with three factors was considered to evaluate the effect of EUDRAGIT ® L100, polyethylene glycol 2000 (PEG 2000) and polysorbate 80 on encapsulation efficiency (EE) of anthocyanins. Also, major parameters of nanoparticles were assessed by using mainly SEM microscopy and Dynamic light scattering. PEG 2000 was the only individual factor that has statistical significance (95% confidence level). The process yields (PY) were found in between 67% and 92%; the particle size and morphology analysis showed two distribution size, one for NPs and another for the agglomerates. The pH-sensitive polymer together with the hydrophilic polymer showed to be suitable as ACNs delivery system. The delayed release profile of ACNs, observed for all formulations, can enhance their poor bioavailability. Nevertheless, ACNs bioavailability in vivo remains to be studied. Copyright© Bentham Science Publishers; For any queries, please email at firstname.lastname@example.org.
Rustioni, Laura; Di Meo, Florent; Guillaume, Maxime; Failla, Osvaldo; Trouillas, Patrick
Anthocyanins are the main grape pigments. Due to their aromatic cyclic arrangements, they are able to absorb the radiation in the low energy range of the visible spectrum. In the fruit of Vitis vinifera L., the five main anthocyanidins (cyanidin, peonidin, delphinidin, petunidin and malvidin) are present as 3-O-glucosides, as well as their acetyl, p-coumaroyl and caffeoyl ester forms. Despite the huge number of experimental studies dedicated to the anthocyanin profile analysis of grapes and wines, the complete theoretical elucidation of the optical properties of grape anthocyanins is missing. The present work carried out this task through quantum chemistry calculations based on time-dependent density functional theory (TD-DFT), compared to experimental spectra. The differences in visible absorption spectra between the most common grape anthocyanins were rationalized according to B-ring substitution, glucosylation and esterification. A particular attention was given to the intra-molecular copigmentation effect, demonstrating the existence of an intra-molecular charge transfer excited state for the p-coumaroyl and caffeoyl ester forms. Copyright © 2013 Elsevier Ltd. All rights reserved.
Lablab purpureus contain bioactive phytochemicals and with potential to be utilized in the pharmaceutical and nutraceutical markets. Ninety four Lablab purpureus accessions are conserved at the USDA, ARS, Plant Genetic Resources Conservation Unit in Griffin, GA. Anthocyanins are present in flowers...
The pH differential method and HPLC are methods that are commonly used by researchers and the food industry for quantifying anthocyanins in a sample. This study was conducted to establish a relationship between the two analytical methods. Seven juice samples containing an array of different individu...
The natural phytochemicals present in foods, including anthocyanins, might play a role in attenuating obesity by producing a decrease in weight and adipose tissue. This review focused on current knowledge about anthocyanins' role in obesity and its related comorbidities reported in animal models and humans. We summarized their target identification and mechanism of action through several pathways and their final effects on health and well-being. Into consideration of ongoing researches, we highlighted the following key points: a healthy relationship between anthocyanin supplementation and antiobesity effects suffers of the same pros and cons evidenced when the beneficial responses to other phytochemical treatments towards different degenerative diseases have been considered; the different dosage applied in animal versus clinical studies; the complex metabolism and biotransformation to which anthocyanins and phytochemicals are subjected in the intestine and tissues; the possibility that different components present in the supplemented mixtures can interact generating antagonistic, synergistic, or additive effects difficult to predict, and the difference between prevention and therapy. The evolution of the field must seriously consider the need to establish new and adequate cellular and animal models which may, in turn, allow the design of more efficient and prevention-targeted clinical studies. PMID:28785373
Anthocyanins consist of a 2-phenylbenzopyrylium moiety with a variety of polyhydroxyl, polymethoxyl, and glycosylated substituents. Their presence is responsible for the red to purplish colors associated with fresh fruits and berries. There is currently a strong interest in these compounds because o...
Anthocyanins consist of a 2-phenylbenzopyrylium moiety with a variety of polyhydroxyl, polymethoxyl, and glycosolated substituents. Their presence is responsible for the red to purplish colors associated with fresh fruits and berries. There is currently a strong interest in these compounds because...
Anthocyanins consist of a 2-phenylbenzopyrylium moiety with a variety of polyhydroxyl, polymethoxyl, and glycosolated substituents. Their presence is responsible for the red to purplish colors associated with fresh fruits and berries. There is currently a strong interest in these compounds because...
Lange, H.; Shropshire, W.; Mohr, H.
Phytochrome (far red form) alone can mediate anthocyanin synthesis in the mustard seedling (Sinapis alba L.). Complete photoreversibility and reciprocity, for both red and far red light exposures over a period of at least 5 minutes, demonstrate this phytochrome involvement. The duration of the initial lag-phase is constant (about 3 hours at 25 C) for seedlings more than 30 hours old and is specific for the system, being independent of the dose or quality of light. Since a complete reversal by far red of a red light induction is possible only during a 5 minute period, phytochrome (far red form) obviously mediates anthocyanin synthesis during the lag-phase although the actual synthesis of pigment can proceed only after the lag-phase is overcome. We suggest that phytochrome (far red form) exerts a double function during the initial lag-phase. It mediates both the build up of a biosynthetic potential (“capacity”) and anthocyanin synthesis. However, the sequence of events leading to anthocyanin is arrested at some intermediate stage until this “capacity” is built up after 3 hours. Once “capacity” is achieved it does not decay readily. Therefore, no significant “secondary lag-phase” occurs if the seedling, under appropriate conditions, is reirradiated after an intervening dark period. The rate or extent of synthesis for both anthocyanin and lipoxygenase, previously reported (32), are functions of the amount of phytochrome (far red form). No “phytochrome paradoxes,” i.e., nonrational relationships between the amount of phytochrome (far red form) and rate or extent of response, were detected. This fact suggests that the mustard seedling is especially well suited for investigating the biophysical and molecular mechanisms of phytochrome action. PMID:16657678
Cortell, Jessica M; Halbleib, Michael; Gallagher, Andrew V; Righetti, Timothy L; Kennedy, James A
The relationships between grapevine (Vitis vinifera) vigor variation and resulting fruit anthocyanin accumulation and composition were investigated. The study was conducted in a commercial vineyard consisting of the same clone, rootstock, age, and vineyard management practices. The experimental design involved assigning vigor zones in two vineyard sites based upon differences in vine growth. Fruits and wines were analyzed by HPLC from designated vigor zones in 2003 and 2004. Average berry weight (grams), average dry skin weight (milligrams), degrees Brix, and pH were higher and titratable acidity (grams per liter) was lower in 2003 compared to 2004. In 2003, only the highest and lowest vigor zones had differences in berry weight, whereas there were no differences in 2004. In both years, high vigor zones had lower degrees Brix and higher titratable acidity (milligrams per liter). Accumulation of anthocyanins (milligrams per berry) was greater in 2003 compared to 2004. There was a trend for lower anthocyanin concentration (milligrams per berry) in high vigor zones in both years. In 2004 compared to 2003, there was a higher proportion of malvidin-3-O-glucoside and lower proportions of the other four anthocyanins (delphinidin-, cyanidin-, petunidin-, and peonidin-3-O-glucosides) found in Pinot Noir. In both years, site A had proportionally higher peonidin-3-O-glucoside and lower malvidin-3-O-glucoside than site B. Some of these differences may be related to the higher exposure and temperatures found in site B compared to site A and also in the low vigor zones.
Veberic, Robert; Stampar, Franci; Schmitzer, Valentina; Cunja, Vlasta; Zupan, Anka; Koron, Darinka; Mikulic-Petkovsek, Maja
The aim of this study was to evaluate the effect of fast and slow freezing and frozen storage on the metabolite content of six blackberry cultivars. The content of metabolites determined with HPLC RI/PDA-MS in stored blackberries was compared with the initial content of the fruit. During frozen storage of fruits a loss of vitamin C up to 80% has been recorded along with changes of color values, which shifted to blue and yellow hues. The color changes were accompanied with increased pH levels and content of anthocyanins. Most of the phenolic groups, sugars, and organic acids showed a better extraction after storage, especially in the slow freezing treatment due to a higher degree of tissue damage by freezing. The 'Thornless Evergreen' cultivar was especially rich in sugars, vitamin C, and phenolic compounds, but the highest levels of anthocyanins were determined in 'Loch Ness' cultivar.
Balestra, C; Cimino, F; Theunissen, S; Snoeck, T; Provyn, S; Canali, R; Bonina, A; Virgili, F
Nutritional antioxidants have been proposed as an expedient strategy to counter the potentially deleterious effects of scuba diving on endothelial function, flow-mediated dilation (FMD) and heart function. Sixteen volunteers performing a single standard dive (20 min at 33 m) according to US Navy diving procedures were randomly assigned to two groups: one was administered with two doses of 200 mg of an anthocyanins (AC)-rich extract from red oranges, 12 and 4 h before diving. Anthocyanins supplementation significantly modulated the effects of diving on haematocrit, body water distribution and FMD. AC administration significantly reduces the potentially harmful endothelial effects of a recreational single dive. The lack of any significant effect on the most common markers of plasma antioxidant capacity suggests that the mechanism underlying this protective activity is independent of the putative antioxidant effect of AC and possibly involves cellular signalling modulation of the response to high oxygen.
Hughes, Nicole M; Morley, Christianna B; Smith, William K
Juvenile leaves in high-light environments commonly appear red as a result of anthocyanin pigments, which play a photoprotective role during light-sensitive ontogenetic stages. The loss of anthocyanin during leaf development presumably corresponds to a decreased need for photoprotection, as photosynthetic maturation allows leaves to utilize higher light intensities. However, the relationship between photosynthetic development and anthocyanin decline has yet to be quantitatively described. In this study, anthocyanin concentration was measured against photopigment content, lamina thickness, anatomical development, and photosynthetic CO(2) exchange in developing leaves of three deciduous tree species. In all species, anthocyanin disappearance corresponded with development of c. 50% mature photopigment concentrations, c. 80% lamina thickness, and differentiation of the mesophyll into palisade and spongy layers. Photosynthetic gas exchange correlated positively with leaf thickness and chlorophyll content, and negatively with anthocyanin concentration. Species with more rapid photosynthetic maturation lost anthocyanin earliest in development. Chlorophyll a/b ratios increased with leaf age, and were lower than those of acyanic species, consistent with a shading effect of anthocyanin. These results suggest that anthocyanin reassimilation is linked closely with chloroplast and whole-leaf developmental processes, supporting the idea that anthocyanins protect tissues until light processing and carbon fixation have matured to balance energy capture with utilization.
Fernandes, I; Marques, C; Évora, A; Cruz, L; de Freitas, V; Calhau, C; Faria, A; Mateus, N
This study was designed to evaluate the pharmacokinetics of Port and table red wine anthocyanins in healthy men. Volunteers were recruited to drink 250 mL of a table red wine (221 mg of anthocyanins) and 150 mL of young Port red wine (49 mg of anthocyanins). Venous blood was collected from participants at 0, 15, 30, 60 and 120 min after wine ingestion. Urine samples were collected at baseline and at 120 min. Anthocyanins and anthocyanin metabolites in plasma and urine samples were quantified by HPLC-DAD and tentatively identified by LC-MS. Red wine anthocyanins were detected in their intact forms in both plasma and urine samples, but the glucuronylated metabolites of peonidin and malvidin (PnGlucr and MvGlucr) were the two main derivatives detected after both red wine consumptions. For the first time, and supported by the synthesis of Mv3Glucr, the main pathway followed by Mv3glc after absorption was described and involves anthocyanidin conjugation with glucuronic acid after glucose removal. Despite the lower total content of anthocyanins ingested when volunteers drank Port wine, no differences were observed in the plasma Cmax of MvGlucr and PnGlucr after table and Port red wine consumption. The relative bioavailability of anthocyanins in Port wine was 96.58 ± 5.74%, compared to the anthocyanins present in red wine. In conclusion, both Port and table red wines are good sources of bioavailable anthocyanins.
Kim, Moonjung; Yoon, Suk Hoo; Jung, Munyhung; Choe, Eunok
This study investigated the stability of meoru (wild vine grape) anthocyanins in the aqueous solution under singlet oxygen. Freeze-dried meoru (1 kg) contained 179.98 mg anthocyanins including delphinidin-3-glucoside, malvidin-3,5-diglucoside, cyanidin-3,5-diglucoside, malvidin-3-glucoside, and cyanidin-3-glucoside. Malvidin-3,5-diglucoside and cyanidin-3-glucoside were the meoru anthocyanins at the highest and the lowest concentration, respectively. Little decrease in total anthocyanins in the aqueous solution was observed in the dark with or without riboflavin, or with light without riboflavin. Singlet oxygen degraded the meoru anthocyanins in the aqueous solution, which suggested chemical quenching of singlet oxygen by the anthocyanins. Degradation of the meoru anthocyanins was structure-dependent; diglucoside anthocyanins were more stable than monoglucoside. And malvidin glucoside was more stable than delphinidin or cyanidin glucoside, which suggested the number of hydroxy groups in the structure was partly related with the anthocyanin stability under singlet oxygen. This is the first report on anthocyanins stability affected by its structure under singlet oxygen.
Khoo, Hock Eng; Azlan, Azrina; Tang, Sou Teng; Lim, See Meng
ABSTRACT Anthocyanins are colored water-soluble pigments belonging to the phenolic group. The pigments are in glycosylated forms. Anthocyanins responsible for the colors, red, purple, and blue, are in fruits and vegetables. Berries, currants, grapes, and some tropical fruits have high anthocyanins content. Red to purplish blue-colored leafy vegetables, grains, roots, and tubers are the edible vegetables that contain a high level of anthocyanins. Among the anthocyanin pigments, cyanidin-3-glucoside is the major anthocyanin found in most of the plants. The colored anthocyanin pigments have been traditionally used as a natural food colorant. The color and stability of these pigments are influenced by pH, light, temperature, and structure. In acidic condition, anthocyanins appear as red but turn blue when the pH increases. Chromatography has been largely applied in extraction, separation, and quantification of anthocyanins. Besides the use of anthocyanidins and anthocyanins as natural dyes, these colored pigments are potential pharmaceutical ingredients that give various beneficial health effects. Scientific studies, such as cell culture studies, animal models, and human clinical trials, show that anthocyanidins and anthocyanins possess antioxidative and antimicrobial activities, improve visual and neurological health, and protect against various non-communicable diseases. These studies confer the health effects of anthocyanidins and anthocyanins, which are due to their potent antioxidant properties. Different mechanisms and pathways are involved in the protective effects, including free-radical scavenging pathway, cyclooxygenase pathway, mitogen-activated protein kinase pathway, and inflammatory cytokines signaling. Therefore, this review focuses on the role of anthocyanidins and anthocyanins as natural food colorants and their nutraceutical properties for health. Abbreviations: CVD: Cardiovascular disease VEGF: Vascular endothelial growth factor PMID:28970777
Flanigan, Patrick M; Niemeyer, Emily D
In this study, we determined the effect of cultivar on total and individual anthocyanin concentrations and phenolic acid levels in eight purple basil varieties and examined the relationship between anthocyanin content, phenolic acid composition, and antioxidant properties. Cultivar had a significant influence on total anthocyanin concentrations as well as individual anthocyanin composition. The four major basil anthocyanins (labelled A-D) were quantified and cultivar had a statistically significant effect on anthocyanins B (p<0.01), C (p<0.01), and D (p<0.01), but not on anthocyanin A (p=0.94). Cultivar did not have a significant effect on total phenolic levels, although it did influence the concentration of some individual phenolic acids, including caftaric (p=0.03) and chicoric (p=0.04) acids. Although total phenolic and anthocyanin levels correlated with measured FRAP antioxidant capacities, for some cultivars the individual phenolic acid and anthocyanin composition was also an important factor affecting the antioxidant properties.
Zhang, Chengshuo; Zhang, Jialin; Li, Xin; Sun, Ning; Yu, Rui; Zhao, Bochao; Yu, Dongyang; Cheng, Ying; Liu, Yongfeng
Huaier aqueous extract, the main active constituent of Huaier proteoglycan, has antihepatocarcinoma activity in experimental and clinical settings. However, the potential and associated antihepatoma mechanisms of Huaier extract are not yet fully understood. Therefore, in this study, we aimed to elucidate the inhibitory proliferation effect of Huaier extract on apoptosis and cycle of HepG2 and Bel-7402 cells. Our data demonstrated that incubation with Huaier extract resulted in a marked decrease in cell viability dose-dependently. Flow cytometric analysis showed that a 48 h treatment of Huaier extract caused cell apoptosis. Typical apoptotic nucleus alterations were observed with fluorescence microscope after Hoechst staining. Immunoblot analysis further demonstrated that Huaier extract activated caspase 3 and PARP. Additionally, Huaier extract inhibited the activity of p-ERK, p-p38, and p-JNK in terms of MAPK. Furthermore, Huaier extract induced HCC cells arrest in S phase and decreased the cycle related protein expression of β-catenin and cyclin D1. Studies with JNK specific inhibitor, SP600125, showed that Huaier extract induced S phase arrest and decreased β-catenin and cyclin D1 expression via JNK signaling pathway. In conclusion, we verify that Huaier extract causes cell apoptosis and induces hepatocellular carcinoma cells arrest in S phase via JNK pathway, which advances our understanding on the molecular mechanisms of Huaier extract in hepatocarcinoma management. PMID:26229542
Cui, Yang; Meng, Hongmei; Liu, Weidong; Wang, Huan; Liu, Qingpeng
In recent years, aqueous extract of Trametes robiniophila Murr. (Huaier), a traditional Chinese medicine, has been frequently used in China for complementary cancer therapy. However, the mechanisms underlying its anticancer effects have yet to be elucidated. The present study aimed to evaluate the ability of Huaier extract to inhibit proliferation, promote apoptosis and suppress mobility in the fibrosarcoma HT1080 cell line in vitro. The cells were treated with gradient doses of Huaier extract at concentrations of 0, 4, 8 or 16 mg/ml for 24, 48 or 72 h. The cell viability and motility were measured in vitro using MTT, invasive, migration and scratch assays. The distribution of the cell cycle and the extent of cellular apoptosis were analyzed by flow cytometry. The apoptotic pathways were detected using a mitochondrial membrane potential transition assay and western blotting. The results revealed that the cellular viability decreased significantly with increasing concentrations of Huaier extract. In addition, cell invasiveness and migration were also suppressed significantly. It was demonstrated that Huaier extract induced G2 cell-cycle arrest and cellular apoptosis in a time- and dose-dependent manner. The decreased mitochondrial membrane potential, the downregulation of B-cell lymphoma 2 and pro-caspase-3, and upregulation of Bcl-2-associated X protein, cleaved caspase-9 and caspase-3 suggested that Huaier extract induced the apoptosis of HT1080 cells through the mitochondrial pathway. The results of the present study indicate that Huaier extract is a potential complementary agent for the treatment of fibrosarcoma.
Yuan, Zuoqing; Zhang, Jianyong; Tu, Changchao; Wang, Zhijing; Xin, Wenpeng
The influence of blueberry anthocyanins on perfluorooctanoic acid (PFOA)-induced stress response in planarian mitochondria was investigated. PFOA at 15mg/L and anthocyanins at 10 or 20mg/L were individually and simultaneously administered to planarians for up to 10d. The results showed PFOA treatment induced an increase in mitochondrial permeability transition pore opening and a decrease antioxidant capacity and enzyme activities. In anthocyanin treated animals, the activity of succinate dehydrogenase, cytochrome oxidase and monoamine oxidase increased, but mitochondrial permeability transition pore opening decreased and total antioxidant capacity increased. An improvement in above-mentioned physiological and biochemical parameters was found in the combined PFOA and anthocyanin treated animals, in a dose-dependent manner. Anthocyanins attenuated the PFOA induced toxicity; antioxidant capacity and enzyme activities are involved in the protective mechanism of anthocyanins. Copyright © 2016 Elsevier Inc. All rights reserved.
Zou, Bo; Wan, Dongli; Li, Ruili; Han, Xiaomin; Li, Guojing; Wang, Ruigang
Anthocyanins, a kind of flavonoid, normally accumulate in the flowers and fruits and make them colorful. Anthocyanin accumulation is regulated via the different temporal and spatial expression of anthocyanin regulatory and biosynthetic genes. CBP60g, a calmodulin binding protein, has previously been shown to have a role in pathogen resistance, drought tolerance and ABA sensitivity. In this study, we found that CBP60g repressed anthocyanin accumulation induced by drought, sucrose and kinetin. The expression pattern of CBP60g was in accordance with the anthocyanin accumulation tissues. Real-time qPCR analysis revealed that the anthocyanin biosynthetic genes CHS, CHI and DFR, as well as two members of MBW complex, PAP1, a MYB transcription factor, and TT8, a bHLH transcription factor, were down regulated by CBP60g. PMID:28253311
Carrillo, Celia; Buvé, Carolien; Panozzo, Agnese; Grauwet, Tara; Hendrickx, Marc
Although natural structural barriers are factors limiting nutrient bioaccessibility, their specific role in anthocyanin bioaccessibility is still unknown. To better understand how natural barriers govern bioactive compound bioaccessibility, an experimental approach comparing anthocyanins and carotenoids was designed, using a single plant matrix. Initial results revealed increased anthocyanin bioaccessibility in masticated black carrot. To explain this observation, samples with increasing levels of bioencapsulation (free-compound, homogenized-puree, puree) were examined. While carotenoid bioaccessibility was inversely proportional to the level of bioencapsulation, barrier disruption did not increase anthocyanin bioaccessibility. This means that mechanical processing is of particular importance in the case of carotenoid bioaccessibility. While micelle incorporation is the limiting factor for carotenoid bioaccessibility, anthocyanin degradation under alkaline conditions in the gastrointestinal tract dominates. In the absence of structural barriers, anthocyanin bioaccessibility is greater than that of carotenoids. Copyright © 2017 Elsevier Ltd. All rights reserved.
Lysenko, Vladimir; Varduny, Tatyana
Chlorophylless flower petals are known to be composed of non-photosynthetic tissues. Here, we show that the light energy storage that can be photoacoustically measured in flower petals of Petunia hybrida is approximately 10-12%. We found that the supposed chlorophylless photosynthesis is an anoxygenic, anthocyanin-dependent process occurring in blue flower petals (ADAPFP), accompanied by non-respiratory light-dependent oxygen uptake and a 1.5-fold photoinduced increase in ATP levels. Using a simple, adhesive tape stripping technique, we have obtained a backside image of an intact flower petal epidermis, revealing sword-shaped ingrowths connecting the cell wall and vacuole, which is of interest for the further study of possible vacuole-related photosynthesis. Approaches to the interpretations of ADAPFP are discussed, and we conclude that these results are not impossible in terms of the known photochemistry of anthocyanins.
Lysenko, Vladimir; Varduny, Tatyana
Chlorophylless flower petals are known to be composed of non-photosynthetic tissues. Here, we show that the light energy storage that can be photoacoustically measured in flower petals of Petunia hybrida is approximately 10-12%. We found that the supposed chlorophylless photosynthesis is an anoxygenic, anthocyanin-dependent process occurring in blue flower petals (ADAPFP), accompanied by non-respiratory light-dependent oxygen uptake and a 1.5-fold photoinduced increase in ATP levels. Using a simple, adhesive tape stripping technique, we have obtained a backside image of an intact flower petal epidermis, revealing sword-shaped ingrowths connecting the cell wall and vacuole, which is of interest for the further study of possible vacuole-related photosynthesis. Approaches to the interpretations of ADAPFP are discussed, and we conclude that these results are not impossible in terms of the known photochemistry of anthocyanins.
Lysenko, Vladimir; Varduny, Tatyana
Chlorophylless flower petals are known to be composed of non-photosynthetic tissues. Here, we show that the light energy storage that can be photoacoustically measured in flower petals of Petunia hybrida is approximately 10-12%. We found that the supposed chlorophylless photosynthesis is an anoxygenic, anthocyanin-dependent process occurring in blue flower petals (ADAPFP), accompanied by non-respiratory light-dependent oxygen uptake and a 1.5-fold photoinduced increase in ATP levels. Using a simple, adhesive tape stripping technique, we have obtained a backside image of an intact flower petal epidermis, revealing sword-shaped ingrowths connecting the cell wall and vacuole, which is of interest for the further study of possible vacuole-related photosynthesis. Approaches to the interpretations of ADAPFP are discussed, and we conclude that these results are not impossible in terms of the known photochemistry of anthocyanins. PMID:24284801
Mancinelli, A L
A comparative study of the spectral sensitivity of anthocyanin production in dark-grown and light-pretreated systems was carried out in Brassica oleracea L., Lycopersicon esculentum Mill., Secale cereale L. and Spirodela polyrrhiza L. Light pretreatments bring about an enhancement of the inductive, red-far red reversible response in all systems, a decrease of the continuous irradiation response in cabbage, rye, and tomato seedlings, and an enhancement of the continuous irradiation response in cabbage leaf disks. Light pretreatments also bring about a marked change in the spectral sensitivity of the continuous irradiation response. The different effect of light pretreatments on the photosensitivity of the response to short and long wavelength irradiations suggests that two photoreceptors, phytochrome and cryptochrome, may be involved in the photoregulation of anthocyanin production.
Vlachojannis, Christian; Zimmermann, Benno F; Chrubasik-Hausmann, Sigrun
Elderberry and chokeberry food supplements may be 'functional food' in patients with metabolic syndrome or influenza but, for this, adequate amounts of co-active ingredients must be consumed in the daily dose. This study aimed to quantify the anthocyanin content in three elderberry and six chokeberry products to assess their usefulness as functional food. Analyses were carried out using an established HPLC procedure. The minimum anthocyanin doses for the treatment of metabolic syndrome disorders were estimated as 110 mg per day and 3.5 g per day for influenza. Three products were inappropriate for clinical use. The lowest liquid supplies were achieved with a proprietary elderberry concentrate (11 mL) and a proprietary chokeberry mother juice (100 mL). Clinical studies are now required to prove the effectiveness and adapt the doses according to the clinical symptoms. Copyright © 2015 John Wiley & Sons, Ltd.
Zhao, Quan; Duan, Chang-Qing; Wang, Jun
Anthocyanins are responsible for the color of grapes and wine, an important attribute of their quality. Many authors have used anthocyanins profile to classify the grape cultivars and wine authenticity. The anthocyanin profiles of grape berries of Vitis amurensis, its hybrids and their wines were analyzed by HPLC-ESI-MS/MS. The results identified 17 anthocyanins in these grape cultivars, including 11 anthocyanin monoglucosides (five pyranoanthocyanin monoglucosides and one acylated pyranoanthocyanin monoglucoside) and six anthocyanin diglucosides. Likewise, 15 kinds of anthocyanins were detected in wines, including six diglucosides and nine monoglucosides of anthocyanidins, in which four pyranoanthocyanin monoglucosides (Petunidin-3-O-glucoside-4-acetaldehyde, Malvidin-3-O-glucoside-4-pyruvic acid, Malvidin-3-O-glucoside-acetaldehyde and Peonidin-3-O-glucoside-4-pyruvic acid) were detected. In addition, a total of 14 kinds of anthocyanins including six diglucosides and eight monoglucosides of anthocyanidins were identified in skins, in which two pyranoanthocyanin monoglucosides (Peonidin-3-O-glucoside-4-pyruvic acid, Malvidin-3-O-glucoside-4-vinylphenol) and one acylated pyranoanthocyanin monoglucoside (Malvidin-3-O-(6-O-acetyl)-glucoside-4-vinylphenol) were detected. The anthocyanins profile of grape skin of V. amurensis and its hybrids consist of the anthocyanin monoglucosides, diglucosides and pyranoanthocyanins. The wines produced resulted in a slightly different anthocyanin distribution. Pelargonidin-3,5-diglucosides was first found in the skins and wines, however, no acetyl was detected in wines. The principal component analysis results suggest that the anthocyanin profiles were helpful to classify these cultivars of V. amurensis. PMID:20559511
Ge, Jingqiu; Hu, Yijie; Wang, Hongxia; Huang, Yuanshe; Zhang, Peng; Liao, Zhihua; Chen, Min
Anthocyanins in purple-fleshed sweet potato (PSP) are beneficial to human health. The leaf color (Lc) gene is a transcription factor involved in regulating anthocyanin biosynthesis. The anthocyanin profiles of wild-type PSP of Ayamurasaki and its three Lc-transgenic lines were investigated by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). In vitro antioxidant activities of wild-type and Lc-transgenic lines, including reducing power activity, DPPH radical scavenging activity, hydroxyl radical scavenging activity, linoleic acid autoxidation inhibition activity, ABTS free radical scavenging activity and oxygen radical absorbance capacity activity, were measured. The results showed that the total anthocyanin contents increased 1.5-1.9 times in three transgenic lines compared with that in wild-type PSP. Seventeen anthocyanins were found in wild-type PSP, while 19 in Lc-transgenic lines including cyanidin-based, peonidin-based and pelargonidin-based anthocyanins. Three pelargonidin-based anthocyanins were detected in three Lc-transgenic lines. Among them, the relative contents of cyanidin-based and pelargonidin-based anthocyanins increased 1.9-2.0 and 3.4-4.5 times respectively, while peonidin-based anthocyanins decreased 1.8-1.9 times in Lc-transgenic lines, compared with wild-type PSP. PSP from wild-type Ayamurasaki and three Lc-transgenic lines exhibited potent antioxidant activities, whereas there was no distinct difference among them. The transgene Lc significantly increased the content of total anthocyanins and remarkably changed the anthocyanin profiles in Ayamurasaki. Such novel and high content of anthocyanins obtained in the Lc-transgenic lines with potent antioxidant activities may provide unique functional products with potential helpful for human health. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.
Xu, Wenping; Peng, Hui; Yang, Tianbao; Whitaker, Bruce; Huang, Luhong; Sun, Jianghao; Chen, Pei
Two diploid woodland strawberry (Fragaria vesca) inbred lines, Ruegen F7-4 (red fruit-bearing) and YW5AF7 (yellow fruit-bearing) were used to study the regulation of anthocyanin biosynthesis in fruit. Ruegen F7-4 fruit had similar total phenolics and anthocyanin contents to commercial octoploid (F. × ananassa) cultivar Seascape, while YW5AF7 exhibited relatively low total phenolics content and no anthocyanin accumulation. Foliar spray of CaCl2 boosted fruit total phenolics content, especially anthocyanins, by more than 20% in both Seascape and RF7-4. Expression levels of almost all the flavonoid pathway genes were comparable in Ruegen F7-4 and YW5AF7 green-stage fruit. However, at the turning and ripe stages, key anthocyanin structural genes, including flavanone 3-hydroxylase (F3H1), dihydroflavonol 4-reductase (DFR2), anthocyanidin synthase (ANS1), and UDP-glucosyltransferase (UGT1), were highly expressed in Ruegen F7-4 compared with YW5AF7 fruit. Calcium treatment further stimulated the expression of those genes in Ruegen F7-4 fruit. Anthocyanins isolated from petioles of YW5AF7 and Ruegen F-7 had the same HPLC-DAD profile, which differed from that of Ruegen F-7 fruit anthocyanins. All the anthocyanin structural genes except FvUGT1 were detected in petioles of YW5AF7 and Ruegen F-7. Taken together, these results indicate that the "yellow" gene in YW5AF7 is a fruit specific regulatory gene(s) for anthocyanin biosynthesis. Calcium can enhance accumulation of anthocyanins and total phenolics in fruit possibly via upregulation of anthocyanin structural genes. Our results also suggest that the anthocyanin biosynthesis machinery in petioles is different from that in fruit. Published by Elsevier Masson SAS.
Li, Boqiang; Xia, Yongxiu; Wang, Yuying; Qin, Guozheng; Tian, Shiping
‘Hongyang’ is a red fleshed kiwifruit with high anthocyanin content. In this study, we mainly investigated effects of different temperatures (25 and 0°C) on anthocyanin biosynthesis in harvested kiwifruit, and characterized the genes encoding key enzymes involved in anthocyanin metabolism, as well as evaluated the mode of the action, by which low temperature regulates anthocyanin accumulation in ‘Hongyang’ kiwifruit during storage period. The results showed that low temperature could effectively enhance the anthocyanin accumulation of kiwifruit in the end of storage period (90 days), which related to the increase in mRNA levels of ANS1, ANS2, DRF1, DRF2, and UGFT2. Moreover, the transcript abundance of MYBA1-1 and MYB5-1, the genes encoding an important component of MYB–bHLH–WD40 (MBW) complex, was up-regulated, possibly contributing to the induction of specific anthocyanin biosynthesis genes under the low temperature. To further investigate the roles of AcMYB5-1/5-2/A1-1 in regulation of anthocyanin biosynthesis, genes encoding the three transcription factors were transiently transformed in Nicotiana benthamiana leaves. Overexpression of AcMYB5-1/5-2/A1-1 activated the gene expression of NtANS and NtDFR in tobacco. Our results suggested that low temperature storage could stimulate the anthocyanin accumulation in harvested kiwifruit via regulating several structural and regulatory genes involved in anthocyanin biosynthesis. PMID:28344589
Zeng, Xue-Qin; Chow, Wah Soon; Su, Li-Juan; Peng, Xin-Xiang; Peng, Chang-Lian
Ten anthocyanin components have been detected in roots of purple sweet potato (Ipomoea batatas Lam.) by high-performance liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry. All the anthocyanins were exclusively cyanidins or peonidin 3-sophoroside-5-glucosides and their acylated derivatives. The total anthocyanin content in purple sweet potato powder obtained by solid-phase extraction was 66 mg g(-1). A strong capacity of purple sweet potato anthocyanins (PSPA) to scavenge reactive oxygen species (superoxide, hydroxyl radical) and the stable 1,1-diphenyl-2-picrylhydrazyl organic free radical was found in vitro using the electron spin resonance technique. To determine the functional roles of anthocyanins in leaves in vivo, for the first time, supplemental anthocyanins were infiltrated into leaves of Arabidopsis thaliana double mutant of the ecotype Landsberg erecta (tt3tt4) deficient in anthocyanin biosynthesis. Chlorophyll fluorescence imaging showed that anthocyanins significantly ameliorated the inactivation of photosystems II during prolonged high-light (1300 micromol m(-2) s(-1)) exposure. Comet assay of DNA revealed an obvious role of supplemental PSPA in alleviating DNA damage by high light in leaves. Our results suggest that anthocyanins could function in vitro and in vivo to alleviate the direct or indirect oxidative damage of the photosynthetic apparatus and DNA in plants caused by high-light stress.
Anderson, Rachel; Ryser, Peter
Several theories exist about the role of anthocyanins in senescing leaves. To elucidate factors contributing to variation in autumn leaf anthocyanin contents among individual trees, we analysed anthocyanins and other leaf traits in 27 individuals of red maple (Acer rubrum L.) over two growing seasons in the context of timing of leaf senescence. Red maple usually turns bright red in the autumn, but there is considerable variation among the trees. Leaf autumn anthocyanin contents were consistent between the two years of investigation. Autumn anthocyanin content strongly correlated with degree of chlorophyll degradation mid to late September, early senescing leaves having the highest concentrations of anthocyanins. It also correlated positively with leaf summer chlorophyll content and dry matter content, and negatively with specific leaf area. Time of leaf senescence and anthocyanin contents correlated with soil pH and with canopy openness. We conclude that the importance of anthocyanins in protection of leaf processes during senescence depends on the time of senescence. Rather than prolonging the growing season by enabling a delayed senescence, autumn anthocyanins in red maple in Ontario are important when senescence happens early, possibly due to the higher irradiance and greater danger of oxidative damage early in the season. PMID:27135339
Anderson, Rachel; Ryser, Peter
Several theories exist about the role of anthocyanins in senescing leaves. To elucidate factors contributing to variation in autumn leaf anthocyanin contents among individual trees, we analysed anthocyanins and other leaf traits in 27 individuals of red maple (Acer rubrum L.) over two growing seasons in the context of timing of leaf senescence. Red maple usually turns bright red in the autumn, but there is considerable variation among the trees. Leaf autumn anthocyanin contents were consistent between the two years of investigation. Autumn anthocyanin content strongly correlated with degree of chlorophyll degradation mid to late September, early senescing leaves having the highest concentrations of anthocyanins. It also correlated positively with leaf summer chlorophyll content and dry matter content, and negatively with specific leaf area. Time of leaf senescence and anthocyanin contents correlated with soil pH and with canopy openness. We conclude that the importance of anthocyanins in protection of leaf processes during senescence depends on the time of senescence. Rather than prolonging the growing season by enabling a delayed senescence, autumn anthocyanins in red maple in Ontario are important when senescence happens early, possibly due to the higher irradiance and greater danger of oxidative damage early in the season.
Kadomura-Ishikawa, Yasuko; Miyawaki, Katsuyuki; Noji, Sumihare; Takahashi, Akira
Anthocyanins are widespread, essential secondary metabolites in higher plants during color development in certain flowers and fruits. In strawberries, anthocyanins are also key contributors to fruit antioxidant capacity and nutritional value. However, the effects of different light qualities on anthocyanin accumulation in strawberry (Fragaria x ananassa, cv. Sachinoka) fruits remain elusive. In the present study, we showed the most efficient increase in anthocyanin content occurred by blue light irradiation. Light sensing at the molecular level was investigated by isolation of two phototropin (FaPHOT1 and FaPHOT2), two cryptochrome (FaCRY1 and FaCRY2), and two phytochrome (FaPHYA and FaPHYB) homologs. Expression analysis revealed only FaPHOT2 transcripts markedly increased depending on fruit developmental stage, and a corresponding increase in anthocyanin content was detected. FaPHOT2 knockdown resulted in decreased anthocyanin content; however, overexpression increased anthocyanin content. These findings suggested blue light induced anthocyanin accumulation, and FaPHOT2 may play a role in sensing blue light, and mediating anthocyanin biosynthesis in strawberry fruits. This is the first report to find a relationship between visible light sensing, and color development in strawberry fruits.
Pliszka, Barbara; Olszewska, Teresa; Drabent, Regina
The fluorescence properties of anthocyanin pigments in extracts of red cabbage, Brassica oleracea, have been studied. The fluorescence spectra and fluorescence excitation spectra have been measured with absorption spectra of anthocyanins in extracts at pH 2 and pH 7. The results of the researches show that kinds of fluorescent anthocyanins (or/and other compounds) depend on pH conditions of red cabbage extracts. The properly chosen parameters of fluorescence measurement allow to distinguish spectrally two different fluorescent anthocyanin compounds in extract at pH 2 in comparison to pH 7, where three fluorescent compounds have been found.
Deineka, V. I.; Deineka, L. A.; Saenko, I. I.
The influence of exchange of HCOOH (System 2) by phosphoric acid (System 1) for acidification of the “acetonitrile–water” mobile phases for reversed-phase HPLC of anthocyanins was investigated in the framework of relative retention analysis. The differences and similarities of anthocyanins separation were revealed. It has been shown that some common features of the quantitative relationships may be used for preliminary anthocyanins structure differentiation, according to the number of OH-groups in anthocyanidin backbone as well as to a number of saccharide molecules in glycoside radicals in position 3 of the anthocyanin without MS detection. PMID:25692073
Jing, Pu; Noriega, Victor; Schwartz, Steven J; Giusti, M Mónica
Purple corn ( Zea mays L.) has been used for centuries as a natural food colorant in South America and, more recently, in Asia and Europe. However, limited information is available on the factors affecting their anthocyanin concentration and profiles. In this study, 18 purple corn samples grown under different conditions in Peru were evaluated for quantitative and qualitative anthocyanin composition as well as total phenolics. High variability was observed on monomeric anthocyanin and phenolic contents with yields ranging from 290 to 1333 mg/100 g dry weight (DW) and from 950 to 3516 mg/100 g DW, respectively, while 30.5-47.1% of the total phenolics were anthocyanins. The major anthocyanins present were cyanidin-3-glucoside, pelargonidin-3-glucoside, peonidin-3-glucoside, cyanidin-3-maloylglucoside, pelargonidin-3-maloylglucoside, and peonidin-3-maloylglucoside, and 35.6-54.0% of the anthocyanins were acylated. Potassium sources/concentrations on the soil and seedling density did not significantly affect anthocyanin composition. The growing location affected anthocyanin levels and the percentage of anthocyanins to total phenolics ( p < 0.01) and should be taken into account when choosing a material for color production.
Lin-Wang, Kui; Micheletti, Diego; Palmer, John; Volz, Richard; Lozano, Lidia; Espley, Richard; Hellens, Roger P; Chagnè, David; Rowan, Daryl D; Troggio, Michela; Iglesias, Ignasi; Allan, Andrew C
The biosynthesis of anthocyanin in many plants is affected by environmental conditions. In apple (Malus × domestica Borkh.), concentrations of fruit anthocyanins are lower under hot climatic conditions. We examined the anthocyanin accumulation in the peel of maturing 'Mondial Gala' and 'Royal Gala' apples, grown in both temperate and hot climates, and using artificial heating of on-tree fruit. Heat caused a dramatic reduction of both peel anthocyanin concentration and transcripts of the genes of the anthocyanin biosynthetic pathway. Heating fruit rapidly reduced expression of the R2R3 MYB transcription factor (MYB10) responsible for coordinative regulation for red skin colour, as well as expression of other genes in the transcriptional activation complex. A single night of low temperatures is sufficient to elicit a large increase in transcription of MYB10 and consequently the biosynthetic pathway. Candidate genes that can repress anthocyanin biosynthesis did not appear to be responsible for reductions in anthocyanin content. We propose that temperature-induced regulation of anthocyanin biosynthesis is primarily caused by altered transcript levels of the activating anthocyanin regulatory complex.
Xu, Jianteng; Su, Xiaoyu; Lim, Soyoung; Griffin, Jason; Carey, Edward; Katz, Benjamin; Tomich, John; Smith, J Scott; Wang, Weiqun
Purple-fleshed sweet potato P40 has been shown to prevent colorectal cancer in a murine model. This study is to identify anthocyanins by using HPLC/MS-MS and assess the stability during various cooking conditions. P40 possesses a high content of anthocyanins up to 14 mg/g dry matter. Total 12 acylated anthocyanins are identified. Top three anthocyanins, e.g., cyanidin 3-caffeoyl-p-hydroxybenzoyl sophoroside-5-glucoside, peonidin 3-caffeoyl sophoroside-5-glucoside, and cyanidin 3-(6"-caffeoyl-6"-feruloylsophoroside)-5-glucoside, account for half of the anthocyanin contents. Over 80% of anthocyanins measured by acid hydrolysis were cyanidin derivatives, indicating P40 is unique when compared with other purple-fleshed sweet potatoes that usually contain more peonidin than cyanidin. Steaming, pressure cooking, microwaving, and frying but not baking significantly reduced 8-16% of total anthocyanin contents. Mono-acylated anthocyanins showed a higher resistance against heat than di- and non-acylated. Among of which, cyanidin 3-p-hydroxybenzoylsophoroside-5-glucoside exhibited the best thermal stability. The stable acylated and cyanidin-predominated anthocyanins in P40 may provide extra benefits for cancer prevention. Copyright © 2014 Elsevier Ltd. All rights reserved.
Wei, Jie; Zhang, Guokun; Zhang, Xiao; Xu, Dexin; Gao, Jun; Fan, Jungang; Zhou, Zhiquan
Aging is the greatest risk factor for most neurodegenerative diseases, which is associated with decreasing cognitive function and significantly affecting life quality in the elderly. Computational analysis suggested that 4 anthocyanins from chokeberry fruit increased Klotho (aging-suppressor) structural stability, so we hypothesized that chokeberry anthocyanins could antiaging. To explore the effects of anthocyanins treatment on brain aging, mice treated with 15 or 30 mg/kg anthocyanins by gavage and injected D-galactose accelerated aging per day. After 8 weeks, cognitive and noncognitive components of behavior were determined. Our studies showed that anthocyanins blocked age-associated cognitive decline and response capacity in senescence accelerated mice. Furthermore, mice treated with anthocyanins-supplemented showed better balance of redox systems (SOD, GSH-PX, and MDA) in all age tests. Three major monoamines were norepinephrine, dopamine, and 5-hydroxytryptamine, and their levels were significantly increased; the levels of inflammatory cytokines (COX2, TGF-β1, and IL-1) transcription and DNA damage were decreased significantly in brains of anthocyanins treated mice compared to aged models. The DNA damage signaling pathway was also regulated with anthocyanins. Our results suggested that anthocyanins was a potential approach for maintaining thinking and memory in aging mice, possibly by regulating the balance of redox system and reducing inflammation accumulation, and the most important factor was inhibiting DNA damage.
Wang, Lingxia; Pan, Dezhuo; Liang, Meng; Abubakar, Yakubu Saddeeq; Li, Jian; Lin, Jinke; Chen, Shipin; Chen, Wei
Plant anthocyanin biosynthesis is well understood, but the regulatory mechanism in purple foliage tea remains unclear. Using isobaric tag for relative and absolute quantification (iTRAQ), 815 differential proteins were identified in the leaves of Zijuan tea, among which 20 were associated with the regulation of anthocyanin metabolism. We found that the abundances of anthocyanin synthesis-related enzymes such as chalcone synthase, chalcone isomerase, dihydroflavonol 4-reductase and anthocyanin synthetase, as well as anthocyanin accumulation-related UDP-glucosyl transferase and ATP-binding cassette (ABC) transporters in the purple leaves were all significantly higher than those in the green leaves. The abundances of the transcription factors bHLH and HY5, regulating anthocyanin biosynthesis at transcriptional level were also obviously higher in purple leaves than those in green leaves. In addition, bifunctional 3-dehydroquinate dehydratase and chorismate mutase in purple leaves were distinctly higher in abundance compared to green leaves, which provided sufficient phenylalanine substrate for anthocyanin synthesis. Furthermore, lignin synthesis was found to be reduced due to the lower abundances of cinnamoyl-CoA reductase 1, peroxidase 15 and laccase-6, which resulted in increase of intermediates flow into anthocyanin synthesis pathway. The physiological data were consistent with proteomic results. These four aspects of biosynthetic regulation contribute to anthocyanin accumulation in purple leaves of Zijuan tea.
Vanzo, Andreja; Terdoslavich, Michela; Brandoni, Anabel; Torres, Adriana M; Vrhovsek, Urska; Passamonti, Sabina
Anthocyanins are among the most common flavonoids in the human diet. In spite of their very low bioavailability, anthocyanins are indicated as active in preventing the progress of cardiovascular and neurodegenerative diseases, obesity, inflammation, and cancer. Any piece of knowledge concerning absorption, tissue distribution, metabolism, and excretion of dietary anthocyanins is expected to help understanding the apparent paradox between their low concentrations in cells and their bioactivity. The aim of this work was to investigate the renal uptake of dietary anthocyanins and the underlying molecular mechanism. A solution containing anthocyanins extracted from grape (Vitis vinifera) was introduced into the isolated stomach of anesthetized rats; after both 10 and 30 min, plasma, liver, and kidney were analyzed for their anthocyanin contents. While anthocyanins in the liver were at apparent equilibrium with plasma both after 10 and 30 min, kidney anthocyanins were 3- and 2.3-fold higher than in plasma, after 10 and 30 min, respectively. Since the transport activity of the bilitranslocase in kidney basolateral membrane vesicles was competitively inhibited by malvidin 3-glucoside (K(i) = 4.8 +/- 0.2 microM), the anthocyanin uptake from blood into kidney tubular cells is likely to be mediated by the kidney isoform of this organic anion membrane transporter.
Ferreira da Silva, Palmira; Lima, João C; Freitas, Adilson A; Shimizu, Karina; Maçanita, Antonio L; Quina, Frank H
Color intensification of anthocyanin solutions in the presence of natural polyphenols (copigmentation) is re-interpreted in terms of charge transfer from the copigment to the anthocyanin. Flavylium cations are shown to be excellent electron acceptors (E(red) approximately -0.3 V vs SCE). It is also demonstrated, for a large series of anthocyanin-copigment pairs, that the standard Gibbs free energy of complex formation decreases linearly with EA(Anthoc) - IP(Cop), the difference between the electron affinity of the anthocyanin, EA(Anthoc), and the ionization potential of the copigment, IP(Cop). Based on this correlation, copigmentation strengths of potential candidates for copigments can be predicted.
Lapidot, T; Harel, S; Akiri, B; Granit, R; Kanner, J
Anthocyanins are one of the main classes of flavonoids in red wines, and they appear to contribute significantly to the powerful antioxidant properties of the flavonoids. In grapes and wines the anthocyanins are in the flavylium form. However, during digestion they may reach higher pH values, forming the carbinol pseudo-base, quinoidal-base, or the chalcone, and these compounds appear to be absorbed from the gut into the blood system. The antioxidant activity of these compounds, in several metal-catalyzed lipid oxidation model systems, was evaluated in comparison with other antioxidants. The pseudo-base and quinoidal-base malvidin 3-glucoside significantly inhibited the peroxidation of linoleate by myoglobin. Both compounds were found to work better than catechin, a well-known antioxidant. In a membrane lipid peroxidation system, the effectiveness of the antioxidant was dependent on the catalyst: In the presence of H(2)O(2)-activated myoglobin, the inhibition efficiency of the antioxidant was malvidin 3-glucoside > catechin > malvidin > resveratrol. However, in the presence of an iron redox cycle catalyzer, the order of effectiveness was resveratrol > malvidin 3-glucoside = malvidin > catechin. The pH-transformed forms of the anthocyanins remained effective antioxidants in these systems, and their I(50) values were between 0.5 and 6.2 microM.
Intuyod, Kitti; Priprem, Aroonsri; Limphirat, Wanwisa; Charoensuk, Lakhanawan; Pinlaor, Porntip; Pairojkul, Chawalit; Lertrat, Kamol; Pinlaor, Somchai
The pharmacological activities of herbal extracts can be enhanced by complex formation. In this study, we manipulated cyanidin and delphinidin-rich extracts to form an anthocyanin complex (AC) with turmeric and evaluated activity against inflammation and periductal fibrosis in Opisthorchis viverrini-infected hamsters. The AC was prepared from anthocyanins extracted from cobs of purple waxy corn (70%), petals of blue butterfly pea (20%) and turmeric extract (10%), resulting in an enhanced free-radical scavenging capacity. Oral administration of AC (175 and 700 mg/kg body weight) every day for 1 month to O. viverrini-infected hamsters resulted in reduced inflammatory cells and periductal fibrosis. Fourier transform infrared spectroscopy and partial least square discriminant analysis suggested nucleic acid changes in the O. viverrini-infected liver samples, which were partially prevented by the AC treatment. AC reduced 8-oxodG formation, an oxidative DNA damage marker, significantly decreased levels of nitrite in the plasma and alanine aminotransferase activity and increased the ferric reducing ability of plasma. AC also decreased the expression of oxidant-related genes (NF-κB and iNOS) and increased the expression of antioxidant-related genes (CAT, SOD, and GPx). Thus, AC increases free-radical scavenging capacity, decreases inflammation, suppresses oxidative/nitrative stress, and reduces liver injury and periductal fibrosis in O. viverrini-infected hamsters.
Blanco-Vega, Dora; Gómez-Alonso, Sergio; Hermosín-Gutiérrez, Isidro
The content and distribution of low molecular weight red wine pigments (anthocyanins, flavanol-anthocyanins adducts and pyranoanthocyanins) has been analysed in 283 wine samples. A total of 90 red wine pigments were identified and up to 68 of them quantified in most of the wine samples. The content of the different pigments classes accounted for wide ranges of values, because of the diversity of the commercial wines regarding grape cultivar and age. Garnacha young wines were prone to contain higher hydroxyphenyl-pyranoanthocyanin concentrations. The aging had an effect of making uniform the concentrations and molar percentages of every type of pigments, and only slight differences among wine groups were found for B-type vitisins (highest values for Syrah wines) and 10-hydroxyphenyl-pyranoanthocyanins (highest values for Merlot wines). Among Tempranillo wines, the ethylidene-bridged flavanol-anthocyanin adducts were the most affected by disappearance during aging, whereas hydroxyphenyl-pyranoanthocyanins increased their contribution in most of those aged wines. Copyright © 2014 Elsevier Ltd. All rights reserved.
Anthocyanin indexes, quercetin, kaempferol, and myricetin may provide industry with potential new medicines or nutraceuticals. Velvetleaf (Abutilon theophrasti Medik) leaves from 42 accessions were analyzed for anthocyanin indexes while both leaves and fruit were used for quercetin, kaempferol, and ...
Sui, Xiaonan; Bary, Solène; Zhou, Weibiao
Many anthocyanin-containing foods are thermally processed to ensure their safety, and stored for some time before being consumed. However, the combination of thermal processing and subsequent storage has a significant impact on anthocyanins. This study aimed to investigate the color, chemical stability, and antioxidant capacity of thermally treated anthocyanin aqueous solutions during storage at 4, 25, 45, and 65 °C, respectively. Anthocyanin aqueous solutions were thermally treated before storage. Results showed that the degradation rate of anthocyanins in aqueous solutions was much faster than those in real food. The color of the anthocyanin aqueous solutions changed dramatically during storage. The anthocyanin aqueous solutions stored at 4 °C showed the best chemical stability. Interestingly, the antioxidant capacity of the anthocyanin aqueous solutions stored at lower temperatures remained the same; however, the antioxidant capacity of those thermally treated at 120 or 140 °C and stored at 45 or 65 °C significantly decreased.
Irani, Niloufer G; Grotewold, Erich
Background Plant pigmentation is affected by a variety of factors. Light, an important plant developmental signal, influences the accumulation of anthocyanins primarily through the activation of the transcription factors that regulate the flavonoid biosynthetic pathway. In this study, we utilized maize Black Mexican Sweet (BMS) cells expressing the R and C1 regulators of anthocyanin biosynthesis from a light-insensitive promoter as a means to investigate the existence of additional levels of control of pigmentation by light. Results BMS cells expressing the R and C1 regulators from the CaMV 35S constitutive promoter accumulate anthocyanins when grown in complete darkness, suggesting that the transcription factors R and C1 are sufficient for the transcription of the genes corresponding to the structural enzymes of the pathway, with no requirement for additional light-induced regulators. Interestingly, light induces a "darkening" in the color of the purple anthocyanin pigmentation of transgenic BMS cells expressing R and C1. This change in the pigment hue is not associated with a variation in the levels or types of anthocyanins present, or with an alteration of the transcript levels of several flavonoid biosynthetic genes. However, cytological observations show that light drives unexpected changes in the morphology and distribution of the anthocyanins-containing vacuolar compartments. Conclusion By uncoupling the effect of light on anthocyanin accumulation, we have found light to induce the fusion of anthocyanin-containing vacuoles, the coalescence of anthocyanic vacuolar inclusion (AVI)-like structures contained, and the spread of anthocyanins from the inclusions into the vacuolar sap. Similar light-induced alterations in vacuolar morphology are also evident in the epidermal cells of maize floral whorls accumulating anthocyanins. Our findings suggest a novel mechanism for the action of light on the vacuolar storage of anthocyanin. PMID:15907203
CUI, YANG; MENG, HONGMEI; LIU, WEIDONG; WANG, HUAN; LIU, QINGPENG
In recent years, aqueous extract of Trametes robiniophila Murr. (Huaier), a traditional Chinese medicine, has been frequently used in China for complementary cancer therapy. However, the mechanisms underlying its anticancer effects have yet to be elucidated. The present study aimed to evaluate the ability of Huaier extract to inhibit proliferation, promote apoptosis and suppress mobility in the fibrosarcoma HT1080 cell line in vitro. The cells were treated with gradient doses of Huaier extract at concentrations of 0, 4, 8 or 16 mg/ml for 24, 48 or 72 h. The cell viability and motility were measured in vitro using MTT, invasive, migration and scratch assays. The distribution of the cell cycle and the extent of cellular apoptosis were analyzed by flow cytometry. The apoptotic pathways were detected using a mitochondrial membrane potential transition assay and western blotting. The results revealed that the cellular viability decreased significantly with increasing concentrations of Huaier extract. In addition, cell invasiveness and migration were also suppressed significantly. It was demonstrated that Huaier extract induced G2 cell-cycle arrest and cellular apoptosis in a time- and dose-dependent manner. The decreased mitochondrial membrane potential, the downregulation of B-cell lymphoma 2 and pro-caspase-3, and upregulation of Bcl-2-associated X protein, cleaved caspase-9 and caspase-3 suggested that Huaier extract induced the apoptosis of HT1080 cells through the mitochondrial pathway. The results of the present study indicate that Huaier extract is a potential complementary agent for the treatment of fibrosarcoma. PMID:25789006
Vepsäläinen, Saila; Koivisto, Henna; Pekkarinen, Elina; Mäkinen, Petra; Dobson, Gary; McDougall, Gordon J; Stewart, Derek; Haapasalo, Annakaisa; Karjalainen, Reijo O; Tanila, Heikki; Hiltunen, Mikko
A growing body of epidemiological evidence suggests that fruit and vegetable juices containing various phenolic compounds can reduce the risk of Alzheimer's disease (AD). As the altered amyloid precursor protein (APP) processing leading to increased β-amyloid (Aβ) production is a key pathogenic feature of AD, we elucidated the effects of different polyphenols on neuroprotection and APP processing under different in vitro stress conditions. The effects of these compounds were also investigated in transgenic AD mice (APdE9). Free radical toxicity and apoptosis were induced in human SH-SY5Y neuroblastoma cells overexpressing APP751. Menadione-induced production of reactive oxygen species was significantly decreased upon treatment with myricetin, quercetin or anthocyanin-rich extracts in a dose-dependent manner. However, these extracts did not affect caspase-3 activation, APP processing or Aβ levels upon staurosporine-induced apoptosis. APdE9 mice fed with anthocyanin-rich bilberry or blackcurrant extracts showed decreased APP C-terminal fragment levels in the cerebral cortex as compared to APdE9 mice on the control diet. Soluble Aβ40 and Aβ42 levels were significantly decreased in bilberry-fed mice as compared to blackcurrant-fed mice. Conversely, the ratio of insoluble Aβ42/40 was significantly decreased in blackcurrant-fed mice relative to bilberry-fed mice. Both berry diets alleviated the spatial working memory deficit of aged APdE9 mice as compared to mice on the control diet. There were no changes in the expression or phosphorylation status of tau in APdE9 mice with respect to diet. These data suggest that anthocyanin-rich bilberry and blackcurrant diets favorably modulate APP processing and alleviate behavioral abnormalities in a mouse model of AD. Copyright © 2013 Elsevier Inc. All rights reserved.
Pratiwi, D. D.; Nurosyid, F.; Supriyanto, A.; Suryana, R.
This article reported combination of anthocyanin and synthetic dyes in dye-sensitized solar cells (DSSC) applications. This study aims was to improve the performance of DSSC by addition of synthetic dye into anthocyanin dye. Anthocyanin dye was extracted from red cabbage and synthetic dye was obtained from N719. We prepared anthocyanin and synthetic dyes at 2 different volume, anthocyanin dye at volume of 10 ml and combination dyes with anthocyanin and synthetic dyes at volume of 8 mL : 2 mL. The DSSCs were designed into sandwich structure on the fluorine-doped tin oxide (FTO) substrates using TiO2 electrode, carbon electrode, anthocyanin and synthetic dyes, and redox electrolyte. The absorption wavelength of anthocyanin dye of red cabbage was 450 nm – 580 nm, the combination of anthocyanin and synthetic dyes can increase the absorbance peak only. The IPCE characteristic with anthocyanin dye of red cabbage and combination dyes resulted quantum efficiency of 0.081% and 0.092% at wavelength maximum about 430 nm. The DSSC by anthocyanin dye of red cabbage achieved a conversion efficiency of 0.024%, while the DSSC by combination dyes achieved a conversion efficiency of 0.054%, combination dyes by addition synthetic dye into anthocyanin dye enhanced the conversion efficiency up to 125%.
Yoshimura, Yukihiro; Zaima, Nobuhiro; Moriyama, Tatsuya; Kawamura, Yukio
Black rice (Oryza sativa L. Japonica) contains high levels of anthocyanins in the pericarp and is considered an effective health-promoting food. Several studies have identified the molecular species of anthocyanins in black rice, but information about the localization of each anthocyanin species is limited because methodologies for investigating the localization such as determining specific antibodies to anthocyanin, have not yet been developed Matrix-assisted laser desorption/ionization imaging mass spectrometry (MALDI-IMS) is a suitable tool for investigating the localization of metabolites. In this study, we identified 7 species of anthocyanin monoglycosides and 2 species of anthocyanin diglycosides in crude extracts from black rice by matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) analysis. We also analyzed black rice sections by MALDI-IMS and found 2 additional species of anthocyanin pentosides and revealed different localization patterns of anthocyanin species composed of different sugar moieties. Anthocyanin species composed of a pentose moiety (cyanidin-3-O-pentoside and petunidin-3-O-pentoside) were localized in the entire pericarp, whereas anthocyanin species composed of a hexose moiety (cyanidin-3-O-hexoside and peonidin-3-O-hexoside) were focally localized in the dorsal pericarp. These results indicate that anthocyanin species composed of different sugar moieties exhibit different localization patterns in the pericarp of black rice. This is the first detailed investigation into the localization of molecular species of anthocyanins by MALDI-IMS. PMID:22363605
UDP-glucosyltransferase (UGT) is a key enzyme during anthocyanin biosynthesis by catalyzing glucosylation of anthocyanins so as to increase their solubility and accumulation. Previously it has been shown that preharvest spray of calcium chloride enhances anthocyanin accumulation in strawberry fruit ...
Ma, Tao; Hu, Na; Ding, Chenxi; Zhang, Qiulong; Li, Wencong; Suo, Yourui; Wang, Honglun; Bai, Bo; Ding, Chenxu
Anthocyanins are the main compounds in Nitraria tangutorun Bobr. The enrichment and purification of anthocyanins on macroporous resins were investigated. Regarding anthocyanin purification, static adsorption and desorption were studied. The optimal experimental conditions were the following: resin type: X-5; static adsorption time: 6h; desorption solution: ethanol-water-HCl (80:19:1, V/V/V; pH 1); desorption time: 40min. Furthermore, the in vitro and in vivo biological activities of the anthocyanins were evaluated. The anthocyanins showed ideal scavenging effects on free radicals in vitro, especially on 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl free radical (OH). In the animal experiment, blood lipid metabolism of hyperlipidemia rats was regulated by anthocyanin contents. The superoxide dismutase (SOD) activity and the total antioxidant capacity (TAC) of hyperlipidemia rats were also improved by anthocyanins. These results showed that anthocyanins from N. tangutorun Bobr. fruits had potential biological activities in vivo as well as in vitro. Copyright © 2015. Published by Elsevier Ltd.
Chung, Cheryl; Rojanasasithara, Thananunt; Mutilangi, William; McClements, David Julian
Anthocyanins are often used in functional foods and beverages as colorants and nutraceuticals. However, these natural compounds may undergo chemical degradation during storage leading to color fading and loss of bioactivity. In particular, vitamin C (l-ascorbic acid) is known to accelerate anthocyanin degradation. In this study, the influence of various food-grade biopolymers on the physical and chemical stability of model beverages containing anthocyanin (0.025%), ascorbic acid (0 or 0.05%), and calcium salt (0 or 0.01%) was examined under accelerated conditions (40°C for 7days). Four biopolymers (1%) were examined for their potential to inhibit anthocyanin degradation: native whey protein; denatured whey protein; citrus pectin; and beet pectin. The physical stability was determined by measuring changes in absorbance, color, and visual appearance. Solutions containing anthocyanin and calcium salt (0 or 0.01%) were stable throughout storage, while those with added ascorbic acid were the least stable. The addition of biopolymers, particularly heat denatured whey protein, significantly enhanced the stability of the anthocyanin during storage. Fluorescence quenching studies showed that the anthocyanin may have formed complexes with the whey protein through hydrogen bonding that resulted in their enhanced stability in the presence of ascorbic acid. This study provides information that may improve the stability of anthocyanins in food and beverage systems. Copyright © 2015 Elsevier Ltd. All rights reserved.
Kirakosyan, Ara; Seymour, E Mitchell; Wolforth, Janet; McNish, Robert; Kaufman, Peter B; Bolling, Steven F
Our aim was to confirm and identify the presence of tart cherry anthocyanins in several target tissues of healthy rats. Liquid chromatography-mass spectrometry analysis was employed for detection and characterisation of anthocyanin metabolites. It was shown that four native anthocyanins, namely cyanidin 3-glucosylrutinoside, cyanidin 3-rutinoside, cyanidin 3-rutinoside 5-β-D-glucoside, and peonidin 3-rutinoside were differentially distributed among targeted tissues of rats. Bladder and kidney contained more total anthocyanins than all other tissues analysed. It was also revealed that the bioavailability pattern of these native anthocyanins among tissues is varied. The highest concentration of individual anthocyanin cyanidin 3-glucosylrutinoside (2339 picograms/gram of tissue) was detected in bladder, followed by cyanidin 3-rutinoside 5-β-d-glucoside (916 picograms/gram) in the liver of rats. Although the diverse distribution of tart cherry anthocyanins in different rat tissues still requires further explanation, it may provide an evidentiary link between tissue bioavailability and health-enhancing properties of anthocyanins at target sites.
Ayed, N.; Yu, H.-L.; Lacroix, M.
This research investigated the effect of gamma irradiation from 0 to 9 kGy, packaging in air or under vacuum, or in combination with other treatments for enhancing anthocyanin extraction from grape pomace. Results indicate that the irradiation at 6 kGy and packaging in the presence of a low concentration of sodium metabisulfite yielded the highest value of anthocyanin extraction.
Higher concentrations of anthocyanins in vegetables are important for attractive appearance and may offer health benefits for consumers. The red color of onion bulbs is due primarily to the accumulation of anthocyanins. Segregating haploid plants from the cross of yellow and red inbreds were asexual...
Anthocyanins are important components to all red colored fruit, but are absolutely crucial for red wine grapes. Despite a century of research, we still have no concrete understanding of how light and temperature impart their effects on anthocyanin accumulation and composition. Our aim was to elucida...
Despite a century of research, we still lack a concrete, mechanistic understanding of solar radiation and temperature effects on anthocyanin accumulation and composition, crucial for red wine grapes. Our aim was to elucidate the mechanistic response to microclimate of anthocyanin metabolism in Viti...
Despite a century of research, we still lack a concrete, mechanistic understanding of solar radiation and temperature effects on anthocyanin accumulation and composition, crucial for red wine grapes. Our aim was to elucidate the mechanistic response to microclimate of anthocyanin metabolism in Viti...
Dietary intervention with anthocyanins may confer benefits in brain function, including vision. Research to date indicates that animals have only a limited capacity to absorb anthocyanins, compared to other types of flavonoids. Pigs, which are a suitable model for human digestive absorption, were us...
Ma, Chunhui; Yang, Lei; Yang, Fengjian; Wang, Wenjie; Zhao, Chunjian; Zu, Yuangang
In this work, a multivariate study based on Box-Behnken Design was used to evaluate the influence of three major variables affecting the performance of the extraction process of Schisandra chinensis anthocyanins. The optimum parameters were 5.5 h extraction time; 1:19 solid-liquid ratio and 260 r/min stirring rate, respectively. The extraction yield of anthocyanins was 29.06 mg/g under the optimum conditions. Moreover, many factors on the impact of heating, ultrasound, microwave treatment and ultraviolet irradiation on content and color stability of anthocyanins from Schisandra chinensis fruit were investigated. The results show that thermal degradation reaction of anthocyanins complies with the first order reaction kinetics, and the correlation coefficient is greater than 0.9950 at 40–80 °C. Ultrasound and microwave treatment has little effect on the stability of anthocyanins, and the extraction time of ultrasound and microwave should be no more than 60 min and 5 min, respectively. The anthocyanins degradation effect of UVC ultraviolet radiation is greater than UVA and UVB; after 9 h ultraviolet radiation, the anthocyanins content degradation of UVC is 23.9 ± 0.7%, and the ΔE* was changed from 62.81 to 76.52 ± 2.3. Through LC-MS analysis, the major composition of Schisandra chinensis anthocyanins was cyanidin-3-O-xylosylrutinoside. PMID:23203065
Curtin, Chris; Zhang, Wei; Franco, Chris
Jasmonic acid altered the accumulation of major anthocyanins in Vitis vinifera cell culture. Peonidin 3-glucoside content at day three was increased from 0.3 to 1.7 mg g(-1) dry cell wt while other major anthocyanins were increased by smaller increments. By day 14, the content of methylated and acylated anthocyanins (peonidin 3-p-coumaroylglucoside and malvidin 3-p-coumaroylglucoside) was 6.3 mg g(-1) DCW, in response to treatment with jasmonic acid, and comprising approximately 45% (w/w) of total anthocyanins. In comparison, the untreated control culture contained 1.2 mg g(-1) DCW which made up approximately 32% (w/w) of total anthocyanins. Light further enhanced anthocyanin accumulation induced by jasmonic acid elicitation. The content of peonidin 3-glucoside at day 3 was 6.6 mg g(-1) DCW, 22-fold higher than control cultures while the content in response to light irradiation alone was 0.6 mg g(-1) DCW. When a highly pigmented cell line was elicited with jasmonic acid total anthocyanins increased from 9.2 to 20.7 mg g(-1) DCW, but there was no change in the anthocyanin composition.
Gould, K S; Markham, K R; Smith, R H; Goris, J J
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.
Bioavailability of anthocyanins from juiced purple carrots was investigated through a human feeding study. Ten healthy adults consumed three doses of purple carrot juice, and bioavailability was assessed by appearance of anthocyanins in plasma for 8 hours after the dose. Doses were 50 mL, 150 mL, ...
Socquet-Juglard, Didier; Bennett, Alexandra A; Manns, David C; Mansfield, Anna Katharine; Robbins, Rebecca J; Collins, Thomas M; Griffiths, Phillip D
The effects of growth temperatures on anthocyanin content and profile were tested on juvenile cabbage and kale plants. The effects of cold storage time were evaluated on both juvenile and mature plants. The anthocyanin content in juvenile plants ranged from 3.82 mg of cyanidin-3,5-diglucoside equivalent (Cy equiv)/g of dry matter (dm) at 25 °C to 10.00 mg of Cy equiv/g of dm at 16 °C, with up to 76% diacylated anthocyanins. Cold storage of juvenile plants decreased the total amount of anthocyanins but increased the diacylated anthocyanin content by 3-5%. In mature plants, cold storage reduced the total anthocyanin content from 22 to 12.23 mg/g after 5 weeks of storage in red cabbage, while the total anthocyanin content increased after 2 weeks of storage from 2.34 to 3.66 mg of Cy equiv/g of dm in kale without having any effect on acylation in either morphotype. The results obtained in this study will be useful for optimizing anthocyanin production.
Wahyuningsih, S.; Wulandari, L.; Wartono, M. W.; Munawaroh, H.; Ramelan, A. H.
Anthocyanins are naturally occurring pigments of red and purple. Red anthocyanin pigments provide a strong and sharp and widely applied in various industries such as food coloring or drink. Anthocyanins isolated by maceration, extraction and thin layer chromatography (TLC). The extract has been obtained from the initial stages of maceration then separated into several fractions by chromatography to isolate fractions colored dark red. Identification of chemical compounds with TLC (Thin Layer Chromatography) is able to distinguish the fraction of anthocyanin produced. FTIR (Fourier Transform Infrared Spectroscopy) used to identification of the functional group of a compound. The UV-Vis absorption spectra have to produce maximum absorbance values that describe the intensity of anthocyanin spectra in different colors for different pH. Anthocyanins are more stable at low pH (acidic conditions) which gives a red pigment. Meanwhile, the higher the pH value of anthocyanin will provide color fading of the color blue. So as a food colorant, anthocyanin with a low pH or height pH has a significant effect on the food colorant.
Shaked-Sachray, Liat; Weiss, David; Reuveni, Moshe; Nissim-Levi, Ada; Oren-Shamir, Michal
Temperature is one of the main external factors affecting anthocyanin accumulation in plant tissues: low temperatures cause an increase and elevated temperatures cause a decrease in anthocyanin concentration. Several metals have been shown to increase the half-life time of anthocyanins, by forming complexes with them. We studied the combined effect of elevated temperatures and increased metal concentrations on the accumulation of anthocyanins in aster 'Sungal' flowers. It has been found that magnesium treatment of aster plants or detached flower buds, partially prevents colour fading at elevated temperatures. Anthocyanin concentration of aster 'Sungal' flowers grown at 29 degrees C/21 degrees C day/night, respectively, was about half that of flowers grown at 17 degrees C/9 degrees C. The activity of phenylalanine ammonia-lyase (PAL) and chalcone isomerase (CHI) decreased as the temperature increased. Treatment of both whole plants and detached flower buds grown at elevated temperatures in the presence of magnesium salts, increased flower anthocyanin concentration by up to 80%. Measurement of magnesium following these treatments revealed an increased level of the metal in the petals, suggesting a direct effect. Magnesium treatment does not seem to cause increased synthesis of anthocyanin through a stress-related reaction, since the activities of both PAL and CHI did not increase due to this treatment. The results of this study show that increasing magnesium levels in aster petals prevents the deleterious effect of elevated temperatures on anthocyanin accumulation, thus enhancing flower colour.
Analysis of anthocyanins responsible for the purple flesh color is important for breeding programs and development of value-added products. This study aimed to optimize the conditions for anthocyanin extraction from purple-fleshed sweet potatoes (PFSP) using pressurized-liquid extraction (PLE) metho...
Strawberry fruit contain phenolic compounds such as anthocyanins, which have beneficial effects against oxidative stress mediated diseases. Two diploid strawberry (Fragaria vesca) inbred lines, Ruegen F7-4 (red fruit) and YW5AF7 (yellow fruit) were used to study the regulation of anthocyanin biosynt...
Concentrations of anthocyanins, phenolic compounds and antioxidant activities in kernels of 20 genotypes of waxy corn were investigated at two maturation stages, namely milky and mature. The levels of anthocyanins increased throughout the development of each genotype of corn, while phenolic compound...
Chanoca, Alexandra; Burkel, Brian; Kovinich, Nik; Grotewold, Erich; Eliceiri, Kevin W; Otegui, Marisa S
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 (τm ) correlated with distinct subcellular localizations of anthocyanins. The vacuolar pool of anthocyanins exhibited shorter τm 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.
Current fruit-based dietary supplements in the US marketplace have no obligation to meet any fruit-component concentration requirement. For example, berry supplements might be promoted for their high anthocyanin content, but they actually have no standard or minimum anthocyanin threshold for legal s...
Ma, Chunhui; Yang, Lei; Yang, Fengjian; Wang, Wenjie; Zhao, Chunjian; Zu, Yuangang
In this work, a multivariate study based on Box-Behnken Design was used to evaluate the influence of three major variables affecting the performance of the extraction process of Schisandra chinensis anthocyanins. The optimum parameters were 5.5 h extraction time; 1:19 solid-liquid ratio and 260 r/min stirring rate, respectively. The extraction yield of anthocyanins was 29.06 mg/g under the optimum conditions. Moreover, many factors on the impact of heating, ultrasound, microwave treatment and ultraviolet irradiation on content and color stability of anthocyanins from Schisandra chinensis fruit were investigated. The results show that thermal degradation reaction of anthocyanins complies with the first order reaction kinetics, and the correlation coefficient is greater than 0.9950 at 40-80°C. Ultrasound and microwave treatment has little effect on the stability of anthocyanins, and the extraction time of ultrasound and microwave should be no more than 60 min and 5 min, respectively. The anthocyanins degradation effect of UVC ultraviolet radiation is greater than UVA and UVB; after 9 h ultraviolet radiation, the anthocyanins content degradation of UVC is 23.9 ± 0.7%, and the ∆E* was changed from 62.81 to 76.52 ± 2.3. Through LC-MS analysis, the major composition of Schisandra chinensis anthocyanins was cyanidin-3-O-xylosylrutinoside.
Anthocyanins are a class of brightly colored, glycosylated flavonoid pigments that imbue their flower, fruit, and vegetable host tissues with hues of predominantly red, purple, and blue. Although all anthocyanins exhibit pH-responsive photochemical changes, distinct structural decorations on the cor...
Rosaceae (strawberry, cherry, blackberry, red raspberry, and black raspberry) dietary supplements and food products (total n=74) were purchased and analyzed to determine their anthocyanin concentrations and profiles. Eight of the 33 dietary supplements had no detectable anthocyanins (five samples) o...
An LC-PDA-ESI/MSn profiling method was used for a comprehensive study of the anthocyanins of purple Bordeaux radish. This study identified 57 anthocyanins: 23 acylated cyanidin 3-sophoroside-5-diglucosides, 12 acylated cyanidin 3-(glucosylacyl) acylsophoroside-5-diglucosides, and 22 acylated cyanid...
Chen, Sha; Xiang, Yue; Deng, Jiao; Liu, Yanling; Li, Shaohua
A validated HPLC-DAD-ESI-MSn method for the analysis of non-anthocyanin flavonoids was applied to nine different tissues of twelve lotus genotypes of Nelumbo nucifera and N. lutea, together with an optimized anthocyanin extraction and separation protocol for lotus petals. A total of five anthocyanins and twenty non-anthocyanin flavonoids was identified and quantified. Flavonoid contents and compositions varied with cultivar and tissue and were used as a basis to divide tissues into three groups characterized by kaempferol and quercetin derivatives. Influences on flower petal coloration were investigated by principal components analyses. High contents of kaempferol glycosides were detected in the petals of N. nucifera while high quercetin glycoside concentrations occurred in N. lutea. Based on these results, biosynthetic pathways leading to specific compounds in lotus tissues are deduced through metabolomic analysis of different genotypes and tissues and correlations among flavonoid compounds. PMID:23646125
Chen, Sha; Xiang, Yue; Deng, Jiao; Liu, Yanling; Li, Shaohua
A validated HPLC-DAD-ESI-MS(n) method for the analysis of non-anthocyanin flavonoids was applied to nine different tissues of twelve lotus genotypes of Nelumbo nucifera and N. lutea, together with an optimized anthocyanin extraction and separation protocol for lotus petals. A total of five anthocyanins and twenty non-anthocyanin flavonoids was identified and quantified. Flavonoid contents and compositions varied with cultivar and tissue and were used as a basis to divide tissues into three groups characterized by kaempferol and quercetin derivatives. Influences on flower petal coloration were investigated by principal components analyses. High contents of kaempferol glycosides were detected in the petals of N. nucifera while high quercetin glycoside concentrations occurred in N. lutea. Based on these results, biosynthetic pathways leading to specific compounds in lotus tissues are deduced through metabolomic analysis of different genotypes and tissues and correlations among flavonoid compounds.
Fossen, Torgils; Øvstedal, Dag Olav
The main anthocyanins from flowers of the orchids Dracula chimaera and D. cordobae were isolated from a purified methanolic extract by preparative HPLC. Their structures were determined to be cyanidin 3-O-(6"-O-malonyl-beta-glucopyranoside), cyanidin 3-O-(6"-O-alpha-rhamnopyranosyl-beta-glucopyranoside), cyanidin 3-O-beta-glucopyranoside, peonidin 3-O-(6"-O-alpha-rhamnopyranosyl-beta-glucopyranoside) and peonidin 3-O-(6"-O-malonyl-beta-glucopyranoside). The structure determinations were mainly based on extensive use of 2D and 1D NMR spectroscopy, UV-vis spectroscopy and MS. The anthocyanin contents of species belonging to the subtribe Pleurothallidinae including genus Dracula Luer (Orchidaceae) have previously not been determined. The high content of anthocyanin rutinosides found in D. chimaera and D. cordobae (78 and 28% of the total anthocyanin content, respectively) differs from previously analysed orchid species, in which glucose is found as the only anthocyanin sugar moiety.
Kuskoski, E Marta; Vega, José M; Rios, José J; Fett, Roseane; Troncoso, Ana M; Asuero, Agustin G
Anthocyanin pigments in the berries of baguaçu (Eugenia umbelliflora Berg), a tropical fruit from Brazil, were extracted with 0.1% HCl in ethanol, and the crude anthocyanin extract was purified by Amberlite XAD-7 open-column chromatography. Six major anthocyanins were isolated by preparative HPLC, and their chemical structures were identified by spectroscopic methods (TLC, UV-vis, MS, and (1)H NMR). Delphinidin 3-O-beta-glucopyranoside, cyanidin 3-O-beta-glucopyranoside, petunidin 3-O-beta-glucopyranoside, pelargonidin 3-O-beta-glucopyranoside, peonidin 3-O-beta-glucopyranoside, and malvidin 3-O-beta-glucopyranoside were identified. On the basis of chromatographic data the total anthocyanin content was 342 mg/100 g of fresh baguaçu berries. Therefore, the concomitant presence of six anthocyanins in a single plant species makes this product promising as a new pigment source.
Wang, Dan; Wang, Xirui; Zhang, Chao; Ma, Yue; Zhao, Xiaoyan
A total of 10 anthocyanin compounds were identified from five purple sweet potato ( Ipomoea batatas L.) varieties, Qunzi, Zishu038, Ji18, Jingshu6, and Ziluolan, by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) to assess their calf thymus DNA-binding ability in vitro. The interaction between anthocyanins and calf thymus DNA in Tris-HCl buffer solution (pH 6.9) was evaluated by fluorescence spectroscopy. Using ethidium bromide (EB) as a fluorescence probe, fluorescence quenching of the emission peak was seen in the DNA-EB system when anthocyanins were added, indicating that the anthocyanins bound with DNA. The acylated groups influenced the ability of the interaction with DNA. Anthocyanins from purple sweet potato with more acylated groups in sorphorose have a stronger binding ability with DNA.
Zhang, K M; Li, Z; Li, Y; Li, Y H; Kong, D Z; Wu, R H
Many plant leaves appear red in the autumn, and many papers have focused on the environmental factors and role of anthocyanin in this process. However few papers have examined the substances that are induced during this process. We hypothesised that excess sugar accumulation directly induces anthocyanin accumulation under autumn conditions. Using two methods (restricting phloem movement and exogenous sucrose feeding), we found that both surplus photosynthate and exogenous sucrose could induce anthocyanin biosynthesis, corresponding to up-regulation of several enzymes involved in anthocyanin biosynthesis (phenylalanine ammonia lyase, chalcone isomerase, dihydroflavonol 4-reductase and flavonoid 3-O-glucosyl transferase) and in transport (glutathione S-transferase). Our results suggest that excess carbohydrate may be the proximate trigger for induction of anthocyanin biosynthesis in autumn, but only when carbohydrates are accumulated for storage.
Maier, Alexander; Hoecker, Ute
In Arabidopsis and many other plant species, anthocyanin pigments accumulate only after light exposure and not in darkness. Excess light of very high fluence rates leads to a further, very strong increase in anthocyanin levels. How excess light is sensed is not well understood. Here, we show that mutations in the key repressor of light signaling, the COP1/SPA complex, cause a strong hyperaccumulation of anthocyanins not only under normal light but also under excess, high light conditions. Hence, normal light signaling via COP1/SPA is required to prevent hyperaccumulation of anthocyanins under these high light conditions. However, since cop1 and spa mutants show a similar high-light responsiveness of anthocyanin accumulation as the wild type it remains to be resolved whether COP1/SPA is directly involved in the high-light response itself.
Putta, Swathi; Yarla, Nagendra Sastry; Peluso, Ilaria; Tiwari, Dinesh Kumar; Reddy, Gorla V; Giri, Priyanka Voori; Kumar, Naresh; Malla, Ramarao; Chari, Veera Brahma; Reddy D, Rama Sekhara; Bade, Ramesh; Mannarapu, Mastan; Barretto, George; Lu, Da-Yong; Tarasov, Vadim V; Chubarev, Vladimir N; Ribeiro, Frederico Fávaro; Scotti, Luciana; Scotti, Marcus T; Kamal, M A; Aliev, Gjumrakch; Rao, Chinthalapally V; Perry, George; Bishayee, Anupam
Anthocyanins belong to the flavonoids class of polyphenols and they are water soluble dark colored natural pigments from fruits and vegetables. Dietary consumption of anthocyanins is high compared to other flavonoids, owing to their wide distribution in plant materials. Anthocyanins are the active component in several herbal folk medicines due to its multifaceted medicinal properties. This review discusses the anthocyanins as multitarget drugs, which posses antioxidant, antidiabetic, antihyperlipidemic, anti inflammatory, anticarcinogenic, antiulcer, cardioprotective, hepatoprotective, neuroprotective role. Several chemotherapeutic activities were observed in vitro and in vivo experimentation on cell-line studies, animal models, and clinical trials. This property of anthocyanins could be promising in providing health benefits against chronic diseases. Copyright© Bentham Science Publishers; For any queries, please email at email@example.com.
Hashimoto, Naoto; Noda, Takahiro; Kim, Sun-Ju; Yamauchi, Hiroaki; Takigawa, Shigenobu; Matsuura-Endo, Chie; Suzuki, Tatsuro; Han, Kyu-Ho; Fukushima, Michihiro
Rats fed a diet containing Shadow Queen (SQ), an anthocyanin-rich potato cultivar, previously showed an increase in the hepatic superoxide dismutase (SOD)-2 mRNA level. We investigated whether an extract of SQ would directly increase the hepatic SOD-2 mRNA level in HepG2 cells. Furthermore, we estimated the intracellular signaling pathway for the induction of SOD-2 mRNA expression. HepG2 cells were stimulated using extracts of four crops, including SQ, for 12 h; only extracts of colored potatoes induced SOD-2 mRNA expression significantly. This induction of SOD-2 mRNA expression was blocked by an inhibitor of the extracellular signal-related kinase (ERK) 1/2 pathway. Furthermore, an extract of SQ increased the phosphorylation of ERK1/2 after 15 or 30 min of stimulation. These data indicate that an extract of SQ directly induces hepatic SOD-2 mRNA expression via activation of ERK1/2 pathway in HepG2 cells.
de Rosas, Inés; Ponce, María Teresa; Malovini, Emiliano; Deis, Leonor; Cavagnaro, Bruno; Cavagnaro, Pablo
Malbec and Bonarda are the two most widely cultivated grape varieties in Argentina, and their derived red wines are recognized worldwide, being their intense color a major quality trait. The temperature during fruit ripening conditions berries color intensity. In the main viticulture region of Malbec and Bonarda a 2-3°C increase in temperature has been predicted for the upcoming years as consequence of the global climate change. In the present study, this predicted temperature raise was simulated under field-crop conditions, and its effect on anthocyanin pigmentation in berries of Malbec and Bonarda was monitored by HPLC analysis throughout the ripening process, in two growing seasons. Additionally, expression levels of regulatory (MYBA1 and MYB4) and structural (UFGT and Vv3AT) anthocyanin genes were monitored in Malbec berry skins. Although cultivar-dependent time-course variation was observed for total anthocyanin content, in general, the berries of both cultivars grown under high temperature (HT) conditions had significantly lower total anthocyanins (∼28-41% reduction), and a higher proportion of acylated anthocyanins, than their respective controls. Expression of MYBA1 and UFGT, but not MYB4, was correlated with anthocyanin pigmentation at half ripening and harvest, whereas overexpression of the acyltransferase gene Vv3AT was associated with higher anthocyanin acylation in HT berries. These results suggest that color development and pigment modifications in Malbec berries under HT are regulated at transcriptional level by MYBA1, UFGT, and Vv3AT genes. These data contribute to the general understanding on the effect of high temperatures on anthocyanin biochemistry and genetic regulation, and may have direct implications in the production of high-quality wines from Malbec and Bonarda.
Vaknin, Hila; Bar-Akiva, Ayelet; Ovadia, Rinat; Nissim-Levi, Ada; Forer, Izhak; Weiss, David; Oren-Shamir, Michal
Anthocyanins are the largest group of plant pigments responsible for colors ranging from red to violet and blue. The biosynthesis of anthocyanins, as part of the larger phenylpropanoid pathway, has been characterized in great detail. In contrast to the detailed molecular knowledge available on anthocyanin synthesis, very little is known about the stability and catabolism of anthocyanins in plants. In this study we present a preliminary characterization of active in planta degradation of anthocyanins, requiring novel mRNA and protein synthesis, in Brunfelsia calycina flowers. Brunfelsia is a unique system for this study, since the decrease in pigment concentration in its flowers (from dark purple to white) is extreme and rapid, and occurs at a specific and well-defined stage of flower development. Treatment of detached flowers with protein and mRNA synthesis inhibitors, at specific stages of flower development, prevented degradation. In addition, treatment of detached flowers with cytokinins delayed senescence without changing the rate of anthocyanin degradation, suggesting that degradation of anthocyanins is not part of the general senescence process of the flowers but rather a distinctive and specific pathway. Based on studies on anthocyanin degradation in wine and juices, peroxidases are reasonable candidates for the in vivo degradation. A significant increase in peroxidase activity was shown to correlate in time with the rate of anthocyanin degradation. An additional indication that oxidative enzymes are involved in the process is the fact that treatment of flowers with reducing agents, such as DTT and glutathione, caused inhibition of degradation. This study represents the first step in the elucidation of the molecular mechanism behind in vivo anthocyanin degradation in plants.
Abdel-Aal, El-Sayed M; Akhtar, Humayoun; Rabalski, Iwona; Bryan, Michael
Anthocyanins are important dietary components with diverse positive functions in human health. This study investigates effects of accelerated solvent extraction (ASE) and microwave-assisted extraction (MAE) on anthocyanin composition and extraction efficiency from blue wheat, purple corn, and black rice in comparison with the commonly used solvent extraction (CSE). Factorial experimental design was employed to study effects of ASE and MAE variables, and anthocyanin extracts were analyzed by spectrophotometry, high-performance liquid chromatography-diode array detector (DAD), and liquid chromatography-mass spectrometry chromatography. The extraction efficiency of ASE and MAE was comparable with CSE at the optimal conditions. The greatest extraction by ASE was achieved at 50 °C, 2500 psi, 10 min using 5 cycles, and 100% flush. For MAE, a combination of 70 °C, 300 W, and 10 min in MAE was the most effective in extracting anthocyanins from blue wheat and purple corn compared with 50 °C, 1200 W, and 20 min for black rice. The anthocyanin composition of grain extracts was influenced by the extraction method. The ASE extraction method seems to be more appropriate in extracting anthocyanins from the colored grains as being comparable with the CSE method based on changes in anthocyanin composition. The method caused lower structural changes in anthocaynins compared with the MAE method. Changes in blue wheat anthocyanins were lower in comparison with purple corn or black rice perhaps due to the absence of acylated anthocyanin compounds in blue wheat. The results show significant differences in anthocyanins among the 3 extraction methods, which indicate a need to standardize a method for valid comparisons among studies and for quality assurance purposes.
Sousa, André; Mateus, Nuno; Silva, Artur Manuel Soares; Vivas, Nicolas; Nonier, Marie-Françoise; Pianet, Isabelle; de Freitas, Victor
Condensation reactions of malvidin-3-glucoside with two representative oak wood furanic aldehydes (furfural and methylfurfural) were conducted in wine-like model solutions. Methylfurfural led to the formation of malvidin-3-glucoside-methylfurfural (603 m/z), whereas furfural led to the formation of malvidin-3-glucoside-furfural (589 m/z). The latter was structurally characterized by 1D and 2D NMR, allowing an elucidation of the formation mechanism of these anthocyanin-furanic aldehyde adducts in the absence of flavanols.
Ring, Ludwig; Yeh, Su-Ying; Hücherig, Stephanie; Hoffmann, Thomas; Blanco-Portales, Rosario; Fouche, Mathieu; Villatoro, Carmen; Denoyes, Béatrice; Monfort, Amparo; Caballero, José Luis; Muñoz-Blanco, Juan; Gershenson, Jonathan; Schwab, Wilfried
Plant phenolics have drawn increasing attention due to their potential nutritional benefits. Although the basic reactions of the phenolics biosynthetic pathways in plants have been intensively analyzed, the regulation of their accumulation and flux through the pathway is not that well established. The aim of this study was to use a strawberry (Fragaria × ananassa) microarray to investigate gene expression patterns associated with the accumulation of phenylpropanoids, flavonoids, and anthocyanins in strawberry fruit. An examination of the transcriptome, coupled with metabolite profiling data from different commercial varieties, was undertaken to identify genes whose expression correlated with altered phenolics composition. Seventeen comparative microarray analyses revealed 15 genes that were differentially (more than 200-fold) expressed in phenolics-rich versus phenolics-poor varieties. The results were validated by heterologous expression of the peroxidase FaPRX27 gene, which showed the highest altered expression level (more than 900-fold). The encoded protein was functionally characterized and is assumed to be involved in lignin formation during strawberry fruit ripening. Quantitative trait locus analysis indicated that the genomic region of FaPRX27 is associated with the fruit color trait. Down-regulation of the CHALCONE SYNTHASE gene and concomitant induction of FaPRX27 expression diverted the flux from anthocyanins to lignin. The results highlight the competition of the different phenolics pathways for their common precursors. The list of the 15 candidates provides new genes that are likely to impact polyphenol accumulation in strawberry fruit and could be used to develop molecular markers to select phenolics-rich germplasm. PMID:23835409
Nakamura, Yuko; Matsumoto, Hitoshi; Morifuji, Masashi; Iida, Hiroyuki; Takeuchi, Yasuo
Black currant anthocyanins consist of delphinidin-3-glucoside (1), delphinidin-3-rutinoside (2), cyanidin-3-glucoside (3), and cyanidin-3-rutinoside (4). A liquid chromatography tandem mass spectrometry method for simultaneous determination of four anthocyanins in human plasma was developed and validated. Samples were prepared using solid phase extraction, followed by chromatographic separation with a reverse phase C(18) column with gradient elution using mobile phases containing water, acetonitrile, and formic acid. The quantification of four anthocyanins was determined by multiple reaction monitoring using electrospray ionization. The method showed good selectivity, sensitivity (limits of quantification for four anthocyanins were 0.2 nmol/L), linearity (0.2-20 nmol/L; r > 0.999), intra- and interday precision, accuracy (<14%), and recovery (62.5-85.7%). Analyte stability was investigated in detail. This method was successfully applied to the determination of delphinidin-3-glucoside (1), delphinidin-3-rutinoside (2), cyanidin-3-glucoside (3), and cyanidin-3-rutinoside (4) concentrations in human plasma after ingestion of a single dose of black currant anthocyanins (87.9 micromol (58.8 mg) total anthocyanins).
Zou, Tangbin; Wang, Dongliang; Guo, Honghui; Zhu, Yanna; Luo, Xiaoqin; Liu, Fengqiong; Ling, Wenhua
Anthocyanins are naturally occurring compounds that impart color to fruits, vegetables, and plants. This study aims to optimize the microwave-assisted extraction (MAE) conditions of anthocyanins from mulberry (M. atropurpurea Roxb.) using response surface methodology (RSM). A Box-Behnken experiment was employed in this regard. Methanol concentration, microwave power, and extraction time were chosen as independent variables. The optimized conditions of MAE were as follows: 59.6% acidified methanol, 425 W power, 25 (v/w) liquid-to-solid ratio, and 132 s time. Under these conditions, 54.72 mg anthocyanins were obtained from 1.0 g mulberry powder. Furthermore, 8 anthocyanins were identified by high-performance liquid chromatography-electrospray ionization-mass spectrometry (HPLC-ESI-MS) in mulberry extract. The results showed that cyanidin-3-glucoside and cyanidin-3-rutinoside are the major anthocyanins in mulberry. In addition, in comparison with conventional extraction, MAE is more rapid and efficient for extracting anthocyanins from mulberry. © 2011 Institute of Food Technologists®
Kuntz, Sabine; Kunz, Clemens; Domann, Eugen; Würdemann, Nora; Unger, Franziska; Römpp, Andreas; Rudloff, Silvia
The anti-inflammatory effects of anthocyanins (ACNs) on vascular functions are discussed controversially because of their low bioavailability. This study was performed to determine whether microorganism (MO)-fermented ACNs influence vascular inflammation in vitro. Therefore, MO growth media were supplemented with an ACN-rich grape/berry extract and growth responses of Escherichia coli, E. faecalis and H. alvei, as well as ACN fermentation were observed. MO supernatants were used for measuring the anti-inflammatory effect of MO-fermented ACNs in an epithelial-endothelial co-culture transwell system. After basolateral enrichment (240 min), endothelial cells were stimulated immediately or after 20 h with TNF-α. Afterwards, leukocyte adhesion, expression of adhesion molecules and cytokine release were measured. Results indicate that E. coli, E. faecalis and H. alvei utilized ACNs differentially concomitant with different anti-inflammatory effects. Whereas E. coli utilized ACNs completely, no anti-inflammatory effects of fermented ACNs were observed on activated endothelial cells. In contrast, ACN metabolites generated by E. faecalis and H. alvei significantly attenuated low-grade stimulated leukocyte adhesion, the expression of adhesion molecules E-selectin, VCAM-1 and ICAM-1 and cytokine secretion (IL-8 and IL-6), as well as NF-κB mRNA expression with a more pronounced effect of E. faecalis than H. alvei. Thus, MO-fermented ACNs have the potential to reduce inflammation. PMID:27384582
Del Bo', Cristian; Cao, Yi; Roursgaard, Martin; Riso, Patrizia; Porrini, Marisa; Loft, Steffen; Møller, Peter
Blueberries are a rich source of anthocyanins (ACNs) and phenolic acids (PA), which are hypothesized to protect against development of atherosclerosis. The present study examined the effect of an ACN- and PA-rich fractions, obtained from a wild blueberry powder, on the capacity to counteract lipid accumulation in macrophages derived from monocytic THP-1 cells. In addition, we tested the capacity of pure ACNs and their metabolites to alter lipid accumulation. THP-1-derived macrophages were incubated with fatty acids (500 μM oleic/palmitic acid, 2:1 ratio) and different concentrations (from 0.05 to 10 μg mL(-1)) of ACN- and PA-rich fractions, pure ACN standards (malvidin, delphinidin and cyanidin 3-glucoside), and metabolites (syringic, gallic and protocatechuic acids). Lipid accumulation was quantified with the fluorescent dye Nile red. Lipid accumulation was reduced at all concentrations of the ACN-rich fraction tested with a maximum reduction at 10 μg mL(-1) (-27.4%; p < 0.0001). The PA-rich fraction significantly reduced the lipid accumulation only at the low concentrations from 0.05 µg mL(-1) to 0.3 µg mL(-1), with respect to the control with fatty acids. Supplementation with pure ACN compounds (malvidin and delphinidin-3-glucoside and its metabolic products (syringic and gallic acid)) reduced lipid accumulation especially at the low concentrations, while no significant effect was observed after cyanidin-3-glucoside and protocatechuic acid supplementation. The results demonstrated a potential role of both the ACN- and PA-rich fractions and single compounds in the lipid accumulation also at concentrations close to that achievable in vivo.
Swimm, Alyson I; Kalman, Daniel
Enteropathogenic Escherichia coli (EPEC) are deadly contaminants in water and food, and induce protrusion of actin-filled membranous pedestals beneath themselves upon attachment to intestinal epithelia. Pedestal formation requires clustering of Tir and subsequent recruitment of cellular tyrosine kinases including Abl, Arg, and Etk as well as signaling molecules Nck, N-WASP, and Arp2/3 complex. We have developed a cytosolic extract-based cellular system that recapitulates actin pedestal formation in permeabilized red blood cells (RBC) infected with EPEC. RBC support attachment of EPEC and translocation of virulence factors, but not pedestal formation. We show here that extract induces a rapid Ca++-dependent release of Tir from the EPEC Type III secretion system, and that cytoplasmic factor(s) present in the extract facilitate translocation of Tir into the RBC plasma membrane. We show that Abl and related kinases in the extract phosphorylate Tir and that actin polymerization can be reconstituted in infected RBC following addition of cytosolic extract. Reconstitution requires the bacterial virulence factors Tir and intimin, and phosphorylation of Tir on tyrosine residue 474 results in the recruitment of Nck, N-WASP, and Arp2/3 complex beneath attached bacteria at sites of actin polymerization. Together these data describe a biochemical system for dissection of host components that mediate Type III secretion and the mechanisms by which complexes of proteins are recruited to discrete sites within the plasma membrane to initiate localized actin polymerization and morphological changes. PMID:18208322
Swimm, Alyson I; Kalman, Daniel
Enteropathogenic Escherichia coli (EPEC) are deadly contaminants in water and food, and induce protrusion of actin-filled membranous pedestals beneath themselves upon attachment to intestinal epithelia. Pedestal formation requires clustering of Tir and subsequent recruitment of cellular tyrosine kinases including Abl, Arg, and Etk as well as signaling molecules Nck, N-WASP, and Arp2/3 complex. We have developed a cytosolic extract-based cellular system that recapitulates actin pedestal formation in permeabilized red blood cells (RBC) infected with EPEC. RBC support attachment of EPEC and translocation of virulence factors, but not pedestal formation. We show here that extract induces a rapid Ca++-dependent release of Tir from the EPEC Type III secretion system, and that cytoplasmic factor(s) present in the extract facilitate translocation of Tir into the RBC plasma membrane. We show that Abl and related kinases in the extract phosphorylate Tir and that actin polymerization can be reconstituted in infected RBC following addition of cytosolic extract. Reconstitution requires the bacterial virulence factors Tir and intimin, and phosphorylation of Tir on tyrosine residue 474 results in the recruitment of Nck, N-WASP, and Arp2/3 complex beneath attached bacteria at sites of actin polymerization. Together these data describe a biochemical system for dissection of host components that mediate Type III secretion and the mechanisms by which complexes of proteins are recruited to discrete sites within the plasma membrane to initiate localized actin polymerization and morphological changes.
Vicentino, Priscila O; Cassella, Ricardo J
This paper proposes a novel approach for the extraction of Hg from Brazilian gasoline samples: extraction induced by microemulsion breaking (EIMB). In this approach, a microemulsion is formed by mixing the sample with n-propanol and HCl. Afterwards, the microemulsion is destabilized by the addition of water and the two phases are separated: (i) the top phase, containing the residual gasoline and (ii) the bottom phase, containing the extracted analyte in a medium containing water, n-propanol and the ethanol originally present in the gasoline sample. The bottom phase is then collected and the Hg is measured by cold vapor atomic absorption spectrometry (CV-AAS). This model study used Brazilian gasoline samples spiked with Hg (organometallic compound) to optimize the process. Under the optimum extraction conditions, the microemulsion was prepared by mixing 8.7mL of sample with 1.2mL of n-propanol and 0.1mL of a 10molL(-1) HCl solution. Emulsion breaking was induced by adding 300µL of deionized water and the bottom phase was collected for the measurement of Hg. Six samples of Brazilian gasoline were spiked with Hg in the organometallic form and recovery percentages in the range of 88-109% were observed.
Vreeburg, Robert A M; van Wezel, Esther E; Ocaña-Calahorro, Francisco; Mes, Jurriaan J
The small intestinal epithelium functions both to absorb nutrients, and to provide a barrier between the outside, luminal, world and the human body. One of the passageways across the intestinal epithelium is paracellular diffusion, which is controlled by the properties of tight junction complexes. We used a differentiated Caco-2 monolayer as a model for small intestinal epithelium to study the effect of crude apple extracts on paracellular permeability. Exposure of crude apple homogenate to the differentiated Caco-2 cells increased the paracellular resistance, determined as trans-epithelial electrical resistance (TEER). This increase was linearly related to the concentration of apple present. The TEER-enhancing effect of apple extract was due to factors mainly present in the cortex, and the induction was not inhibited by protein kinase inhibitors. Apple-induced resistance was accompanied by increased expression of several tight junction related genes, including claudin 4 (CLDN4). Crude apple extract induces a higher paracellular resistance in differentiated Caco-2 cells. Future research will determine whether these results can be extrapolated to human small intestinal epithelia. Copyright © 2011 Society of Chemical Industry.
Bonfili, Laura; Amici, Manila; Cecarini, Valentina; Cuccioloni, Massimiliano; Tacconi, Rosalia; Angeletti, Mauro; Fioretti, Evandro; Keller, Jeffrey N; Eleuteri, Anna Maria
Natural occurring modulators of proteasome functionality are extensively investigated for their implication in cancer therapy. On the basis of our previous evidences both on proteasomal inhibition by monomeric polyphenols, and on the characterization of wheat sprout hydroalcoholic extract, herein we thoroughly report on a comparative study of the effect of wheat sprout extract on both normal and tumour cells. Treatment of isolated 20S proteasomes with wheat sprout extracts induced a gradual inhibition of all proteasome activities. Next, two wheat sprout extract components were separated: a polyphenol and a protein fraction. Both components exerted an in vitro inhibitory effect on proteasome activity. HeLa tumour cells and FHs 74 Int normal cells were exposed to both fractions, resulting in different rates of proteasome inhibition, with tumour cells showing a significantly higher degree of proteasome impairment and apoptosis induction. Furthermore, a decrease in proteasome activities and in cell survival of the human plasmacytoma RPMI 8226 cell line, upon the same treatments, was observed. Collectively, our results provide additional evidences supporting the possible use of natural extracts as coadjuvants in cancer treatments.
LANGE, INGO; MOSCHNY, JULIA; TAMANYAN, KAMILLA; KHUTSISHVILI, MANANA; ATHA, DANIEL; BORRIS, ROBERT P.; KOOMOA, DANA-LYNN
Effective neuroblastoma (NB) treatments are still limited despite treatment options available today. Therefore, this study attempted to identify novel plant extracts that have anticancer effects. Cytotoxicity and increased intracellular calcium levels were determined using the Sulforhodamine B (SRB) assay and Fluo4-AM (acetoxymethyl) staining and fluorescence microscopy in NB cells in order to screen a library of plant extracts. The current study examined the anticancer effects of a dichloromethane extract from Scrophularia orientalis L. (Scrophulariaceae), a plant that has been used in Traditional Chinese Medicine. This extract contained highly potent agents that significantly reduced cell survival and increased calcium levels in NB cells. Further analysis revealed that cell death induced by this extract was associated with intracellular calcium release, opening of the MPTP, caspase 3- and PARP-cleavage suggesting that this extract induced aberrant calcium signaling that resulted in apoptosis via the mitochondrial pathway. Therefore, agents from Scrophularia orientalis may have the potential to lead to new chemo therapeutic anticancer drugs. Furthermore, targeting intracellular calcium signaling may be a novel strategy to develop more effective treatments for NB. PMID:26848085
Wu, Kuei-Meng; Yao, Jiaqin; Boring, Daniel
Recent chronic toxicity studies performed on green tea extracts in fasted dogs have revealed some unique dose-limiting lethal liver, gastrointestinal, and renal toxicities. Key findings included necrosis of hepatic cells, gastrointestinal epithelia and renal tubules, atrophy of reproductive organs, atrophy and necrosis of hematopoietic tissues, and associated hematological changes. The polyphenol cachetins (a mixture of primarily epigallocatechin gallate [≥55%]; plus up to 10% each of epigallocatechin, epicatechin, and epigallocatechin gallate) appeared to be the causative agents for the observed toxicities because they are the active ingredients of green tea extract studied. Conduct of the study in nonfasted dogs under the same testing conditions and dose levels showed unremarkable results. Assuming both studies were valid, at the identified no observed adverse effect levels (NOAEL) of each study, systemic exposures (based on area under the curve [AUC]) were actually lower in fasted than nonfasted dogs, suggesting that fasting may have rendered the target organ systems potentially more vulnerable to the effects of green tea extract. The toxicity mechanisms that produced lethality are not known, but the results are scientifically intriguing. Because tea drinking has become more popular in the United States and abroad, the mode of action and site of action of green tea extract-induced lethal toxicities during fasting and the role of other phytochemical components of Folia Camellia sinensis (including nonpolyphenol fractions, which are often consumed when whole-leaf products are presented) warrant further investigation.
Martello, M D; David, N; Matuo, R; Carvalho, P C; Navarro, S D; Monreal, A C D; Cunha-Laura, A L; Cardoso, C A L; Kassuya, C A L; Oliveira, R J
Campomanesia adamantium (Cambess.) O. Berg. is originally from Brazil. Its leaves and fruits have medicinal properties such as anti-inflammatory, antidiarrheal and antiseptic properties. However, the mutagenic potential of this species has been reported in few studies. This study describes the mutagenic/antimutagenic, splenic phagocytic, and apoptotic activities of C. adamantium hydroethanolic extract with or without cyclophosphamide in Swiss mice. The animals orally received the hydroethanolic extract at doses of 30, 100, or 300 mg/kg with or without 100 mg/kg cyclophosphamide. Mutagenesis was evaluated by performing the micronucleus assay after treatment for 24, 48, and 72 h, while splenic phagocytic and apoptotic effects were investigated after 72 h. Short-term exposure of 30 and 100 mg/kg extract induced mild clastogenic/aneugenic effects and increased splenic phagocytosis and apoptosis in the liver, spleen, and kidneys. When the extract was administered in combination with cyclophosphamide, micronucleus frequency and apoptosis reduced. Extract components might affect cyclophosphamide metabolism, which possibly leads to increased clearance of this chemotherapeutic agent. C. adamantium showed mutagenic activity and it may decrease the effectiveness of drugs with metabolic pathways similar to those associated with cyclophosphamide. Thus, caution should be exercised while consuming these extracts, especially when received in combination with other drugs.
Assadollahi, V; Gholami, M; Zendedel, A
The aim of this study was to evaluate the effect of C. zeylanicum aqueous extract on cell growth in the human myelocytic leukemia cell line (THP-1). Today, application of Cinnamon for treatment of cancer investigates extensively. Cinnamon has antioxidant, anti-apoptotic and anti-inflammatory properties. In this experimental study, THP-1 was incubated in 2, 1, 0.1 and 0.01 mg/ml C. zeylanicum solutions for 24, 48 and 72 hours. Cell cycle was assessed with flow cytometry. Apoptotic cells were identified by Hoechst 33342 staining. Cell proliferation was assessed by the MTT assay. The data were analyzed using descriptive statistics and analytical tests. Samples that supplemented with 0.1 mg/ml C. zeylanicum aqueous extract enhanced induction of apoptosis in THP-1 cell line compared to samples that supplemented with 2, 1 and 0.01 mg/ml. According to flow cytometry analysis, after 24 and 72 hours of incubation in 0.1 and 2 mg/ml C. zeylanicum aqueous extract, respectively, the amount of cells in apoptosis phase was higher than that in the control sample. Supplemented C. zeylanicum aqueous extract induced apoptosis in the human myelocytic leukemia cell line (Fig. 4, Ref. 20).
Zsivanovits, G.; Ludneva, D.; Iliev, A.
Anthocyanin contents of fruits were estimated by VIS spectrophotometer and compared with spectra measured by NIR spectrophotometer (600-1100 nm step 10 nm). The aim was to find a relationship between NIR method and traditional spectrophotometric method. The testing protocol, using NIR, is easier, faster and non-destructive. NIR spectra were prepared in pairs, reflectance and transmittance. A modular spectrocomputer, realized on the basis of a monochromator and peripherals Bentham Instruments Ltd (GB) and a photometric camera created at Canning Research Institute, were used. An important feature of this camera is the possibility offered for a simultaneous measurement of both transmittance and reflectance with geometry patterns T0/180 and R0/45. The collected spectra were analyzed by CAMO Unscrambler 9.1 software, with PCA, PLS, PCR methods. Based on the analyzed spectra quality and quantity sensitive calibrations were prepared. The results showed that the NIR method allows measuring of the total anthocyanin content in fresh berry fruits or processed products without destroying them.
Deikman, J.; Hammer, P. E.
Arabidopsis thaliana plants treated with exogenous cytokinins accumulate anthocyanin pigments. We have characterized this response because it is potentially useful as a genetic marker for cytokinin responsiveness. Levels of mRNAs for four genes of the anthocyanin biosynthesis pathway, phenylalanine ammonia lyase 1 (PAL1), chalcone synthase (CHS), chalcone isomerase (CHI), and dihydroflavonol reductase (DFR) were shown to increase coordinately in response to benzyladenine (BA). However, nuclear run-on transcription experiments suggested that although CHS and DFR are controlled by BA at the transcriptional level, PAL1 and CHI are controlled by BA posttranscriptionally. CHS mRNA levels increased within 2 h of BA spray application, and peaked by 3 h. Levels of PAL1 mRNA did not increase within 6 h of BA spray. We also showed that PAL1, CHS, CHI, and DFR mRNA levels fluctuate during a 24-h period and appear to be controlled by a circadian clock. The relation between cytokinin regulation and light regulation of CHS gene transcription is discussed. PMID:12228453
Kang, Soo-Young; Seeram, Navindra P; Nair, Muraleedharan G; Bourquin, Leslie D
Anthocyanins, which are bioactive phytochemicals, are widely distributed in plants and especially enriched in tart cherries. Based on previous observations that tart cherry anthocyanins and their respective aglycone, cyanidin, can inhibit cyclooxygenase enzymes, we conducted experiments to test the potential of anthocyanins to inhibit intestinal tumor development in Apc(Min) mice and growth of human colon cancer cell lines. Mice consuming the cherry diet, anthocyanins, or cyanidin had significantly fewer and smaller cecal adenomas than mice consuming the control diet or sulindac. Colonic tumor numbers and volume were not significantly influenced by treatment. Anthocyanins and cyanidin also reduced cell growth of human colon cancer cell lines HT 29 and HCT 116. The IC(50) of anthocyanins and cyanidin was 780 and 63 microM for HT 29 cells, respectively and 285 and 85 microM for HCT 116 cells, respectively. These results suggest that tart cherry anthocyanins and cyanidin may reduce the risk of colon cancer.
Cui, Baolu; Hu, Zongli; Zhang, Yanjie; Hu, Jingtao; Yin, Wencheng; Feng, Ye; Xie, Qiaoli; Chen, Guoping
Lablab pods, as dietary vegetable, have high nutritional values similar to most of edible legumes. Moreover, our studies confirmed that purple lablab pods contain the natural pigments of anthocyanins and flavonols. Compared to green pods, five kinds of anthocyanins (malvidin, delphinidin and petunidin derivatives) were found in purple pods by HPLC-ESI-MS/MS and the major contents were delphinidin derivatives. Besides, nine kinds of polyphenol derivatives (quercetin, myricetin, kaempferol and apigenin derivatives) were detected by UPLC-ESI-MS/MS and the major components were quercetin and myricetin derivatives. In order to discover their molecular mechanism, expression patterns of biosynthesis and regulatory gens of anthocyanins and flavonols were investigated. Experimental results showed that LpPAL, LpF3H, LpF3'H, LpDFR, LpANS and LpPAP1 expressions were significantly induced in purple pods compared to green ones. Meanwhile, transcripts of LpFLS were more abundant in purple pods than green or yellow ones, suggestind that co-pigments of anthocyanins and flavonols are accumulated in purple pods. Under continuously dark condition, no anthocyanin accumulation was detected in purple pods and transcripts of LpCHS, LpANS, LpFLS and LpPAP1 were remarkably repressed, indicating that anthocyanins and flavonols biosynthesis in purple pods was regulated in light-dependent manner. These results indicate that co-pigments of anthocyanins and flavonols contribute to purple pigmentations of pods.
Tian, Ji; Jin, Kaina; Yao, Yuncong
Anthocyanin is a critical factor involved in coloration of plant tissues, but the mechanism how medium pH values affect anthocyanin accumulation in woody plants is unknown. We analyzed anthocyanin composition and the expression of elements encoding anthocyanin and flavonols biosynthesis underlying different medium pH values by using three different leave color type cultivars. HPLC analysis demonstrated that high medium pH values treatment induced a dramatic decrease in the concentration of cyaniding in crabapple leaves. Conversely, the high medium pH values induced up-regulation of the content of flavones and flavonols, suggesting that low pH treatment-induced anthocyanin accumulation. Quantitative real time PCR experiment showed the expression level of anthocyanidin synthase (McANS) and uridine diphosphate glucose flavonoid 3-O-glucosyltransferase (McUFGT) was up-regulated by low pH values treatment, and high medium pH value treatment up-regulate the transcription level of flavonol synthase (McFLS). Meanwhile, several MYB TFs have been suggested in the regulation of pH responses. These results strongly indicate that the low pH treatment-induced anthocyanin accumulation is mediated by the variation of mRNA transcription of the anthocyanin biosynthetic genes. PMID:24914811
Zhang, Yanchen; Zhang, Jie; Song, Tingting; Li, Jinyan; Tian, Ji; Jin, Kaina; Yao, Yuncong
Anthocyanin is a critical factor involved in coloration of plant tissues, but the mechanism how medium pH values affect anthocyanin accumulation in woody plants is unknown. We analyzed anthocyanin composition and the expression of elements encoding anthocyanin and flavonols biosynthesis underlying different medium pH values by using three different leave color type cultivars. HPLC analysis demonstrated that high medium pH values treatment induced a dramatic decrease in the concentration of cyaniding in crabapple leaves. Conversely, the high medium pH values induced up-regulation of the content of flavones and flavonols, suggesting that low pH treatment-induced anthocyanin accumulation. Quantitative real time PCR experiment showed the expression level of anthocyanidin synthase (McANS) and uridine diphosphate glucose flavonoid 3-O-glucosyltransferase (McUFGT) was up-regulated by low pH values treatment, and high medium pH value treatment up-regulate the transcription level of flavonol synthase (McFLS). Meanwhile, several MYB TFs have been suggested in the regulation of pH responses. These results strongly indicate that the low pH treatment-induced anthocyanin accumulation is mediated by the variation of mRNA transcription of the anthocyanin biosynthetic genes.
Albert, Nick W.
The synthesis of anthocyanin pigments and proanthocyanidins (condensed tannins) is regulated by MYB-bHLH-WDR (MBW) transcription factor complexes in all angiosperms studied to date. Tr-MYB133 and Tr-MYB134 were isolated from Trifolium repens and encode R2R3-MYBs that antagonize the activity of MBW activation complexes. These two genes are conserved in other legume species, and form two sub-clades within the larger anthocyanin/proanthocyanidin clade of MYB repressors. However, unlike petunia and Arabidopsis, these R2R3-MYB repressors do not prevent ectopic accumulation of anthocyanins or proanthocyanidins. Instead, they are expressed when anthocyanins or proanthocyanidins are being synthesized, and provide feedback regulation to MBW complexes. This feedback occurs because Tr-MYB133 and Tr-MYB134 are themselves regulated by MBW complexes. Tr-MYB133 is regulated by MBW complexes containing anthocyanin-related R2R3-MYB proteins (Tr-RED LEAF), while Tr-MYB134 is regulated by complexes containing the proanthocyanidin R2R3-MYBs (Tr-MYB14). Other features of the MBW gene regulation networks are also conserved within legumes, including the ability for the anthocyanin MBW complexes to activate the expression of the AN1/TT8 clade bHLH factor. The regulation of Tr-MYB133 and Tr-MYB134 by distinct, pathway-specific MBW complexes has resulted in subspecialization for controlling anthocyanin or proanthocyanidin synthesis. PMID:26779194
Kamiloglu, Senem; Capanoglu, Esra; Grootaert, Charlotte; Van Camp, John
Anthocyanins from different plant sources have been shown to possess health beneficial effects against a number of chronic diseases. To obtain any influence in a specific tissue or organ, these bioactive compounds must be bioavailable, i.e., effectively absorbed from the gut into the circulation and transferred to the appropriate location within the body while still maintaining their bioactivity. One of the key factors affecting the bioavailability of anthocyanins is their transport through the gut epithelium. The Caco-2 cell line, a human intestinal epithelial cell model derived from a colon carcinoma, has been proven to be a good alternative to animal studies for predicting intestinal absorption of anthocyanins. Studies investigating anthocyanin absorption by Caco-2 cells report very low absorption of these compounds. However, the bioavailability of anthocyanins may be underestimated since the metabolites formed in the course of digestion could be responsible for the health benefits associated with anthocyanins. In this review, we critically discuss recent findings reported on the anthocyanin absorption and metabolism by human intestinal Caco-2 cells.
Chaudhary, Bratati; Mukhopadhyay, Kunal
Anthocyanins are plant pigments that are potential candidates for use as natural food colourant. In this study, Syzygium cumini fruit skin has been used as anthocyanin source. All the six major types of anthocyanins were identified in the sample by ultra performance liquid chromatography studies, and the antioxidant activity was found to be 4.34 ± 0.26 Fe(2+)g(- 1) in the sample with highest anthocyanin content. Optimization of conditions for extracting high amounts of anthocyanin from the fruit peels was investigated by response surface methodology. The results suggested that highest anthocyanin yield (763.80 mg; 100 ml(- 1)), highest chroma and hue angle in the red colour range could be obtained when 20% ethanol was used in combination with 1% acetic acid. Methanol was replaced with ethanol for the extraction of pigments due to its less toxicity and being safe for human consumption. The optimized solvent can be used to extract anthocyanins from the S. cumini fruits and used as natural colourants in the food industries.
Kamiloglu, Senem; Capanoglu, Esra; Grootaert, Charlotte; Van Camp, John
Anthocyanins from different plant sources have been shown to possess health beneficial effects against a number of chronic diseases. To obtain any influence in a specific tissue or organ, these bioactive compounds must be bioavailable, i.e., effectively absorbed from the gut into the circulation and transferred to the appropriate location within the body while still maintaining their bioactivity. One of the key factors affecting the bioavailability of anthocyanins is their transport through the gut epithelium. The Caco-2 cell line, a human intestinal epithelial cell model derived from a colon carcinoma, has been proven to be a good alternative to animal studies for predicting intestinal absorption of anthocyanins. Studies investigating anthocyanin absorption by Caco-2 cells report very low absorption of these compounds. However, the bioavailability of anthocyanins may be underestimated since the metabolites formed in the course of digestion could be responsible for the health benefits associated with anthocyanins. In this review, we critically discuss recent findings reported on the anthocyanin absorption and metabolism by human intestinal Caco-2 cells. PMID:26370977
Wang, Zhaoran; Li, Yuan; Chen, Liang; Xin, Xiulan; Yuan, Qipeng
Anthocyanins are well-known antioxidants, but they are sensitive to environmental conditions. Herein we used oxidized starch microgel to prevent their early degradation and deliver them to the target place. The aim of this study was to investigate the uptake and the release ability of anthocyanins by the oxidized starch microgels and measure their in vitro gastrointestinal release. The gels were made of oxidized potato starch polymers, which were chemically cross-linked by sodium trimetaphosphate (STMP). In this study, the uptake and release behaviors of anthocyanins by starch microgel were investigated under various pH and salt concentrations. The microgel of high degree of oxidation and high cross-link density had a high uptake capacity for anthocyanins at low pH and salt concentration; 62 mg anthocyanins had been absorbed per gram of dry DO100% (degree of oxidation 100%) microgel at pH 3 with ionic strength 0.05M. The in vitro study of the release was investigated under stimulated gastrointestinal fluid. The anthocyanins were identified and quantified by UV/vis detection. The results indicated that the oxidized starch microgels had a potential for being a carrier system for protecting anthocyanins from degradation in the upper gastric tract and for delivering them to the intestine. This paper provides a good reference for an intestinal-targeted delivery system of vulnerable functional ingredients by oxidized starch microgel.
Meng, Lai-Sheng; Li, Ying-Qiu; Liu, Meng-Qian; Jiang, Ji-Hong
Anthocyanin accumulation specifically depends on sucrose (Suc) signaling/levels. However, the gene cascades specifically involved in the Suc signaling/level-mediated anthocyanin biosynthetic pathway are still unknown. Arabidopsis ANGUSTIFOLIA3 (AN3), a transcription coactivator, is involved in the regulation of leaf shape and drought tolerance. Recently, an AN3-CONSTITUTIVE PHOTOMORPHOGENIC 1 gene cascade has been reported to regulate the light signaling-mediated anthocyanin accumulation. Target gene analysis indicates that AN3 is associated with the YODA (YDA) promoter, a mitogen-activated protein kinase kinase kinase, in vivo for inducing anthocyanin accumulation. Indeed, loss-of-function mutants of YDA showed significantly increased anthocyanin accumulation. YDA mutation can also suppress the decrease in an3-4 anthocyanin accumulation. Further analysis indicates that the mutations of AN3 and YDA disrupt the normal Suc levels because of the changes of invertase activity in mutants of an3 or yda, which in turn induces the alterations of anthocyanin accumulation in mutants of an3 or yda via unknown regulatory mechanisms. PMID:27920784
Li, Huayin; Li, Jingjuan; Zhang, Yihui
Anthocyanin in strawberries has a positive effect on fruit coloration. In this study, the role of exogenous hematin on anthocyanin biosynthesis was investigated. Our result showed that the white stage of strawberries treated with exogenous hematin had higher anthocyanin content, compared to the control group. Among all treatments, 5 μM of hematin was the optimal condition to promote color development. In order to explore the molecular mechanism of fruit coloring regulated by hematin, transcriptomes in the hematin- and non-hematin-treated fruit were analyzed. A large number of differentially expressed genes (DEGs) were identified in regulating anthocyanin synthesis, including the DEGs involved in anthocyanin biosynthesis, hormone signaling transduction, phytochrome signaling, starch and sucrose degradation, and transcriptional pathways. These regulatory networks may play an important role in regulating the color process of strawberries treated with hematin. In summary, exogenous hematin could promote fruit coloring by increasing anthocyanin content in the white stage of strawberries. Furthermore, transcriptome analysis suggests that hematin-promoted fruit coloring occurs through multiple related metabolic pathways, which provides valuable information for regulating fruit color via anthocyanin biosynthesis in strawberries. PMID:28074176
Liao, Jingjing; Zang, Jian; Yuan, Fei; Liu, Shuang; Zhang, Yibo; Li, Haiyan; Piao, Zhongyun; Li, Hongbo
Fruit color is an important index and parameter for measuring fruit quality. As an important pigment, anthocyanin is a determinant which appears in all sorts of colors of fruits in nature. Color parameters were measured using a spectrometer and used as a basis to divide the materials into three groups: reddish-orange, orange and yellow. A validated high-performance liquid chromatographic-electrospray ionization-mass spectrometric method was used for the analysis of anthocyanin in Schisandra chinensis and for determining major anthocyanin components in S. chinensis fruits, i.e. cyanidin xylosyl-glucoside (CyXylGlu), cyanidin glucosyl-rutinoside (CyGluRutin), cyanidin rutinoside (CyRutin) and cyanidin xylosyl-rutinoside (CyXylRutin). The anthocyanin contents vary obviously in different colored fruits in S. chinensis. The impact of anthocyanin on coloration of fruits was investigated by multiple regression analysis between color parameters and anthocyanin components, which indicated that CyRutin is the primary cause of fruit color variation in S. chinensis. The content and type of anthocyanin determine fruit coloration in S. chinensis, laying the early foundations for systematically interpreting the mechanism of fruit coloration in S. chinensis. © 2015 Society of Chemical Industry. © 2015 Society of Chemical Industry.
Zipor, Gadi; Duarte, Patrícia; Carqueijeiro, Inês; Shahar, Liat; Ovadia, Rinat; Teper-Bamnolker, Paula; Eshel, Dani; Levin, Yishai; Doron-Faigenboim, Adi; Sottomayor, Mariana; Oren-Shamir, Michal
In contrast to detailed knowledge regarding the biosynthesis of anthocyanins, the largest group of plant pigments, little is known about their in planta degradation. It has been suggested that anthocyanin degradation is enzymatically controlled and induced when beneficial to the plant. Here we investigated the enzymatic process in Brunfelsia calycina flowers, as they changed color from purple to white. We characterized the enzymatic process by which B. calycina protein extracts degrade anthocyanins. A candidate peroxidase was partially purified and characterized and its intracellular localization was determined. The transcript sequence of this peroxidase was fully identified. A basic peroxidase, BcPrx01, is responsible for the in planta degradation of anthocyanins in B. calycina flowers. BcPrx01 has the ability to degrade complex anthocyanins, it co-localizes with these pigments in the vacuoles of petals, and both the mRNA and protein levels of BcPrx01 are greatly induced parallel to the degradation of anthocyanins. Both isoelectric focusing (IEF) gel analysis and 3D structure prediction indicated that BcPrx01 is cationic. Identification of BcPrx01 is a significant breakthrough both in the understanding of anthocyanin catabolism in plants and in the field of peroxidases, where such a consistent relationship between expression levels, in planta subcellular localization and activity has seldom been demonstrated. © 2014 The Authors. New Phytologist © 2014 New Phytologist Trust.
Singh, Bal Ram
Anthocyanins are a group of plant antioxidants known for their therapeutic use. The effects of natural light, red light, and far-red light on individual as well as total anthocyanin content in cranberry fruit (Vaccinium macrocarpon Ait) were examined in an experimental setting designed to mimic water-harvesting conditions. The reversed-phase high-performance liquid chromatography (HPLC) method was used to separate and analyze the anthocyanins. In contrast to the case of the control sample that was kept in the dark, natural light increased the total anthocyanin level by 75.3% and 87.2% after 24 and 48 hours of water immersion, respectively. Red light and far-red light increased the total anthocyanin level by 41.5% and 34.7%, respectively. The amount of each individual anthocyanin increased differently under natural light, red light, and far-red light, suggesting that expressions of enzymes that catalyze the anthocyanin biosynthesis are regulated differently by environments. PMID:15577187
Zhang, Yongqiang; Liu, Zhongjuan; Liu, Jianping; Lin, Sheng; Wang, Jianfeng; Lin, Wenxiong; Xu, Weifeng
DELLA proteins positively regulate nitrogen deficiency-induced anthocyanin accumulation through directly interaction with PAP1 to enhance its transcriptional activity on anthocyanin biosynthetic gene expressions. Plants can survive a limiting nitrogen supply by undergoing adaptive responses, including induction of anthocyanin production. However, the detailed mechanism is still unclear. In this study, we found that this process was impaired and enhanced, respectively, by exogenous GA3 (an active form of GAs) and paclobutrazol (PAC, a specific GA biosynthesis inhibitor) in Arabidopsis seedlings. Consistently, the nitrogen deficiency-induced transcript levels of several key genes involved in anthocyanin biosynthesis, including F3'H, DFR, LDOX, and UF3GT, were decreased and enhanced by exogenous GA3 and PAC, respectively. Moreover, the nitrogen deficiency-induced anthocyanin accumulation and biosynthesis gene expressions were impaired in the loss-of-function mutant gai-t6/rga-t2/rgl1-1/rgl2-1/rgl3-1 (della) but enhanced in the GA-insensitive mutant gai, suggesting that DELLA proteins, known as repressors of GA signaling, are necessary for fully induction of nitrogen deficiency-driven anthocyanin biosynthesis. Using yeast two-hybrid (Y2H) assay, pull-down assay, and luciferase complementation assay, it was found that RGA, a DELLA of Arabidopsis, could strongly interact with PAP1, a known regulatory transcription factor positively involved in anthocyanin biosynthesis. Furthermore, transient expression assays indicated that RGA and GAI could enhance the transcriptional activities of PAP1 on its downstream genes, including F3'H and DFR. Taken together, this study suggests that DELLAs are necessary regulators for nitrogen deficiency-induced anthocyanin accumulation through interaction with PAP1 and enhancement of PAP1's transcriptional activity on its target genes. GA-DELLA-involved anthocyanin accumulation is important for plant adaptation to nitrogen deficiency.
Ellis, Tom J.; Field, David L.
Background and aims Angiosperms display remarkable diversity in flower colour, implying that transitions between pigmentation phenotypes must have been common. Despite progress in understanding transitions between anthocyanin (blue, purple, pink or red) and unpigmented (white) flowers, little is known about the evolutionary patterns of flower-colour transitions in lineages with both yellow and anthocyanin-pigmented flowers. This study investigates the relative rates of evolutionary transitions between different combinations of yellow- and anthocyanin-pigmentation phenotypes in the tribe Antirrhineae. Methods We surveyed taxonomic literature for data on anthocyanin and yellow floral pigmentation for 369 species across the tribe. We then reconstructed the phylogeny of 169 taxa and used phylogenetic comparative methods to estimate transition rates among pigmentation phenotypes across the phylogeny. Key Results In contrast to previous studies we found a bias towards transitions involving a gain in pigmentation, although transitions to phenotypes with both anthocyanin and yellow taxa are nevertheless extremely rare. Despite the dominance of yellow and anthocyanin-pigmented taxa, transitions between these phenotypes are constrained to move through a white intermediate stage, whereas transitions to double-pigmentation are very rare. The most abundant transitions are between anthocyanin-pigmented and unpigmented flowers, and similarly the most abundant polymorphic taxa were those with anthocyanin-pigmented and unpigmented flowers. Conclusions Our findings show that pigment evolution is limited by the presence of other floral pigments. This interaction between anthocyanin and yellow pigments constrains the breadth of potential floral diversity observed in nature. In particular, they suggest that selection has repeatedly acted to promote the spread of single-pigmented phenotypes across the Antirrhineae phylogeny. Furthermore, the correlation between transition rates and
Ellis, Tom J; Field, David L
Angiosperms display remarkable diversity in flower colour, implying that transitions between pigmentation phenotypes must have been common. Despite progress in understanding transitions between anthocyanin (blue, purple, pink or red) and unpigmented (white) flowers, little is known about the evolutionary patterns of flower-colour transitions in lineages with both yellow and anthocyanin-pigmented flowers. This study investigates the relative rates of evolutionary transitions between different combinations of yellow- and anthocyanin-pigmentation phenotypes in the tribe Antirrhineae. We surveyed taxonomic literature for data on anthocyanin and yellow floral pigmentation for 369 species across the tribe. We then reconstructed the phylogeny of 169 taxa and used phylogenetic comparative methods to estimate transition rates among pigmentation phenotypes across the phylogeny. In contrast to previous studies we found a bias towards transitions involving a gain in pigmentation, although transitions to phenotypes with both anthocyanin and yellow taxa are nevertheless extremely rare. Despite the dominance of yellow and anthocyanin-pigmented taxa, transitions between these phenotypes are constrained to move through a white intermediate stage, whereas transitions to double-pigmentation are very rare. The most abundant transitions are between anthocyanin-pigmented and unpigmented flowers, and similarly the most abundant polymorphic taxa were those with anthocyanin-pigmented and unpigmented flowers. Our findings show that pigment evolution is limited by the presence of other floral pigments. This interaction between anthocyanin and yellow pigments constrains the breadth of potential floral diversity observed in nature. In particular, they suggest that selection has repeatedly acted to promote the spread of single-pigmented phenotypes across the Antirrhineae phylogeny. Furthermore, the correlation between transition rates and polymorphism suggests that the forces causing and
Zhang, Jiangli; Chen, Changsheng; Zhang, Di; Li, Houhua; Li, Pengmin; Ma, Fengwang
Solar ultraviolet irradiation regulates anthocyanin synthesis in apple peel by modulating the production of reactive oxygen species via plasma membrane NADPH oxidase instead of other pathways. The synthesis of anthocyanin in apple peels is dependent upon solar irradiation. Using 3-mm commercial glass to attenuate solar UV-A and UV-B light, we confirmed that solar UV irradiation regulated anthocyanin synthesis in apple peels after exposing previously bagged fruit to sunlight. During sunlight exposure, UV attenuation did not affect the expression of MdHY5, MdCOP1, or MdCRY2, but significantly lowered plasma membrane NADPH oxidase activity and superoxide anion concentrations. UV attenuation also reduced the expression levels of MdMYB10, MdPAL, MdCHS, MdF3H, MdDFR, MdANS and MdUFGT1, UDP-glycose:flavonoid 3-O-glycosyltransferase (UFGT) activity, and local concentrations of anthocyanin and quercetin-3-glycoside. In contrast, exogenous application of hydrogen peroxide could enhance anthocyanin and quercetin-3-glycoside synthesis. Xanthophyll cycle pool size on a chlorophyll basis was higher but its de-epoxidation was lower under direct sunlight irradiation than that under UV-attenuating conditions. This suggests that reactive oxygen species (ROS) produced in chloroplast are not major contributors to anthocyanin synthesis regulation. Inhibition of plasma membrane NADPH oxidase activity lowered the production of ROS through this mechanism, significantly inhibited the synthesis of anthocyanin, and increased the total production of ROS in apple peel under direct sunlight irradiation, suggesting that ROS produced via plasma membrane NADPH oxidase regulates anthocyanin synthesis. In summary, solar UV irradiation regulated anthocyanin synthesis in apple peels by modulating the production of ROS via plasma membrane NADPH oxidase.
Jeong, Seok-Won; Das, Prasanta Kumar; Jeoung, Sae Chae; Song, Ji-Young; Lee, Hyun Kyoung; Kim, Yeon-Ki; Kim, Woo Jung; Park, Yong Il; Yoo, Sang-Dong; Choi, Sang-Bong; Choi, Giltsu; Park, Youn-Il
Anthocyanin accumulation is regulated negatively by ethylene signaling and positively by sugar and light signaling. However, the antagonistic interactions underlying these signalings remain to be elucidated fully. We show that ethylene inhibits anthocyanin accumulation induced by sucrose (Suc) and light by suppressing the expression of transcription factors that positively regulate anthocyanin biosynthesis, including GLABRA3, TRANSPARENT TESTA8, and PRODUCTION OF ANTHOCYANIN PIGMENT1, while stimulating the concomitant expression of the negative R3-MYB regulator MYBL2. Genetic analyses show that the ethylene-mediated suppression of anthocyanin accumulation is dependent upon ethylene signaling components responsible for the triple response. Furthermore, these positive and negative signaling pathways appear to be under photosynthetic control. Suc and light induction of anthocyanin accumulation was almost fully inhibited in wild-type Arabidopsis (Arabidopsis thaliana) ecotype Columbia and ethylene (ethylene response1 [etr1-1]) and light (long hypocotyl1 [hy1], cryptochrome1/2, and hy5) signaling mutants treated with the photosynthetic electron transport inhibitor 3-(3,4-dichlorophenyl)-1,1-dimethylurea. The transcript level of the sugar transporter gene SUC1 was enhanced in ecotype Columbia treated with the ethylene-binding inhibitor silver and in etr1-1, ethylene insensitive2 (ein2-1), and ein3 ein3-like1 mutants. In contrast, 3-(3,4-dichlorophenyl)-1,1-dimethylurea treatment reduced SUC1 expression, which indicates strongly that SUC1 represents an integrator for signals provided by sugar, light, and ethylene. SUC1 mutations lowered accumulations of anthocyanin pigment, soluble sugar content, and ethylene production in response to Suc and light signals. These data demonstrate that the suppression of SUC1 expression by ethylene inhibits Suc-induced anthocyanin accumulation in the presence of light and, hence, fine-tunes anthocyanin homeostasis. PMID:20876338
Yi, Weiguang; Akoh, Casimir C; Fischer, Joan; Krewer, Gerard
Recent studies have shown that dietary polyphenols may contribute to the prevention of cardiovascular disease and cancer. Anthocyanins from different plant sources including blueberries have been shown to possess potential anticancer activities. One of the key factors needed to correctly relate the in vitro study results to human disease outcomes is information about bioavailability. The objectives of the current study were to evaluate the absorption of blueberry anthocyanin extracts using Caco-2 human intestinal cell monolayers and investigate the effects of different aglycones, sugar moieties, and chemical structure on bioavailability of different types of anthocyanins. The results of this study showed that anthocyanins from blueberries could be transported through the Caco-2 cell monolayers although the transport/absorption efficiency was relatively low compared to other aglycone polyphenols. The transport efficiency of anthocyanins averaged approximately 3-4% [less than 1% in delphinidin glucoside (Dp-glc)]. No significant difference in transport/absorption efficiency was observed among three blueberry cultivars. The observed trends among different anthocyanins generally agreed well with some published in vivo results. Dp-glc showed the lowest transport/absorption efficiency, and malvidin glucoside (Mv-glc) showed the highest transport/absorption efficiency. Our result indicates that more free hydroxyl groups and less OCH(3) groups can decrease the bioavailability of anthocyanins. In addition, cyanindin glucoside (Cy-glc) showed significantly higher transport efficiency than cyanidin galactoside (Cy-gal), and peonidin glucoside (Pn-glc) showed significantly higher transport efficiency than peonidin galactoside (Pn-gal), indicating that glucose-based anthocyanins have higher bioavailability than galactose-based anthocyanins.
Cheng, Jun; Wei, Guochao; Zhou, Hui; Gu, Chao; Vimolmangkang, Sornkanok; Liao, Liao; Han, Yuepeng
Modification of anthocyanin plays an important role in increasing its stability in plants. Here, six anthocyanins were identified in peach (Prunus persica), and their structural diversity is attributed to glycosylation and methylation. Interestingly, peach is quite similar to the wild species Prunus ferganensis but differs from both Prunus davidiana and Prunus kansueasis in terms of anthocyanin composition in flowers. This indicates that peach is probably domesticated from P. ferganensis. Subsequently, genes responsible for both methylation and glycosylation of anthocyanins were identified, and their spatiotemporal expression results in different patterns of anthocyanin accumulation in flowers, leaves, and fruits. Two tandem-duplicated genes encoding flavonoid 3-O-glycosyltransferase (F3GT) in peach, PpUGT78A1 and PpUGT78A2, showed different activity toward anthocyanin, providing an example of divergent evolution of F3GT genes in plants. Two genes encoding anthocyanin O-methyltransferase (AOMT), PpAOMT1 and PpAOMT2, are expressed in leaves and flowers, but only PpAOMT2 is responsible for the O-methylation of anthocyanins at the 3′ position in peach. In addition, our study reveals a novel branch of UGT78 genes in plants that lack the highly conserved intron 2 of the UGT gene family, with a great variation of the amino acid residue at position 22 of the plant secondary product glycosyltransferase box. Our results not only provide insights into the mechanisms underlying anthocyanin glycosylation and methylation in peach but will also aid in future attempts to manipulate flavonoid biosynthesis in peach as well as in other plants. PMID:25106821
Sasaki, Nobuhiro; Nakayama, Toru
Genetic engineering of roses and other plants of floricultural importance to give them a truly blue petal color is arguably one of the holy grails of plant biotechnology. Toward this goal, bluish carnations and roses were previously engineered by establishing an exclusive accumulation of delphinidin (Dp)-type anthocyanins in their petals via the heterologous expression of a flavonoid 3',5'-hydroxylase gene. Very recently, purple-blue varieties of chrysanthemums were also genetically engineered via a similar biochemical strategy. Although the floral colors of these transgenic plants still lack a true blue color, the basis for the future molecular breeding of truly blue flowers is via the engineering of anthocyanin pathways. Anthocyanins with multiple aromatic acyl groups (often referred to as polyacylated anthocyanins) in the 3'- or 7-position tend to display a more stable blue color than non-acylated anthocyanins. The 7-polyacylation process during the biosynthesis of purple-blue anthocyanins in delphinium (Delphinium grandiflorum) was found to occur in vacuoles using acyl-glucose as both the glucosyl and acyl donor. Glucosyltransferases and acyltransferases involved in anthocyanin 7-polyacylation in delphinium are vacuolar acyl-glucose-dependent enzymes belonging to the glycoside hydrolase family 1 and serine carboxypeptidae-like protein family, respectively. The 7-polyacylation proceeds through the alternate glucosylation and p-hydroxybenzoylation catalyzed by these enzymes. p-Hydroxybenzoyl-glucose serves as the p-hydroxybenzoyl and glucosyl donor to produce anthocyanins modified with a p-hydroxybenzoyl-glucose concatemer at the 7-position. This novel finding has provided a potential breakthrough for the genetic engineering of truly blue flowers, where polyacylated Dp-type anthocyanins are accumulated exclusively in the petals.
Gomez Roldan, Maria Victoria; Outchkourov, Nikolay; van Houwelingen, Adèle; Lammers, Michiel; Romero de la Fuente, Irene; Ziklo, Noa; Aharoni, Asaph; Hall, Robert D; Beekwilder, Jules
Anthocyanins contribute to the appearance of fruit by conferring to them a red, blue or purple colour. In a food context, they have also been suggested to promote consumer health. In purple tomato tissues, such as hypocotyls, stems and purple fruits, various anthocyanins accumulate. These molecules have characteristic patterns of modification, including hydroxylations, methylations, glycosylations and acylations. The genetic basis for many of these modifications has not been fully elucidated, and nor has their role in the functioning of anthocyanins. In this paper, AnthOMT, an O-methyltransferase (OMT) mediating the methylation of anthocyanins, has been identified and functionally characterized using a combined metabolomics and transcriptomics approach. Gene candidates were selected from the draft tomato genome, and their expression was subsequently monitored in a tomato seedling system comprising three tissues and involving several time points. In addition, we also followed gene expression in wild-type red and purple transgenic tomato fruits expressing Rosea1 and Delila transcription factors. Of the 57 candidates identified, only a single OMT gene showed patterns strongly correlating with both accumulation of anthocyanins and expression of anthocyanin biosynthesis genes. This candidate (AnthOMT) was compared to a closely related caffeoyl CoA OMT by recombinant expression in Escherichia coli, and then tested for substrate specificity. AnthOMT showed a strong affinity for glycosylated anthocyanins, while other flavonoid glycosides and aglycones were much less preferred. Gene silencing experiments with AnthOMT resulted in reduced levels of the predominant methylated anthocyanins. This confirms the role of this enzyme in the diversification of tomato anthocyanins.
Asenstorfer, Robert E; Morgan, Anne L; Hayasaka, Yoji; Sedgley, Margaret; Jones, Graham P
A new method has been developed for the isolation and rapid identification of anthocyanins from two floricultural crops based on the use of high-voltage paper electrophoresis with bisulphite buffer. Using this method, anthocyanin pigments were successfully purified as their negatively charged bisulphite-addition compounds from crude extracts of plant tissue. In conjunction with liquid chromatography-electrospray mass spectrometry, the method enabled the anthocyanins from the flowers of two Banksia species and the leaves of two Acacia species to be identified. The Banksia flowers contained both cyanidin and peonidin-based pigments, while the Acacia leaves contained cyanidin and delphinidin derivatives.
Lin, Haixia; Guo, Xiaoqing; Zhang, Suhui; Dial, Stacey L; Guo, Lei; Manjanatha, Mugimane G; Moore, Martha M; Mei, Nan
Ginkgo biloba has been used for many thousand years as a traditional herbal remedy and its extract has been consumed for many decades as a dietary supplement. Ginkgo biloba leaf extract is a complex mixture with many constituents, including flavonol glycosides and terpene lactones. The National Toxicology Program 2-year cancer bioassay found that G. biloba leaf extract targets the liver, thyroid gland, and nose of rodents; however, the mechanism of G. biloba leaf extract-associated carcinogenicity remains unclear. In the current study, the in vitro genotoxicity of G. biloba leaf extract and its eight constituents was evaluated using the mouse lymphoma assay (MLA) and Comet assay. The underlying mechanisms of G. biloba leaf extract-associated genotoxicity were explored. Ginkgo biloba leaf extract, quercetin, and kaempferol resulted in a dose-dependent increase in the mutant frequency and DNA double-strand breaks (DSBs). Western blot analysis confirmed that G. biloba leaf extract, quercetin, and kaempferol activated the DNA damage signaling pathway with increased expression of γ-H2AX and phosphorylated Chk2 and Chk1. In addition, G. biloba leaf extract produced reactive oxygen species and decreased glutathione levels in L5178Y cells. Loss of heterozygosity analysis of mutants indicated that G. biloba leaf extract, quercetin, and kaempferol treatments resulted in extensive chromosomal damage. These results indicate that G. biloba leaf extract and its two constituents, quercetin and kaempferol, are mutagenic to the mouse L5178Y cells and induce DSBs. Quercetin and kaempferol likely are major contributors to G. biloba leaf extract-induced genotoxicity.
Robaina, Nicolle F; Feiteira, Fernanda N; Cassella, Alessandra R; Cassella, Ricardo J
The present paper reports on the development of a novel extraction induced by emulsion breaking (EIEB) method for the determination of chloride in crude oils. The proposed method was based on the formation and breaking of oil-in-water emulsions with the samples and the consequential transference of the highly water-soluble chloride to the aqueous phase during emulsion breaking, which was achieved by centrifugation. The determination of chloride in the extracts was performed by ion chromatography (IC) with conductivity detection. Several parameters (oil phase:aqueous phase ratio, crude oil:mineral oil ratio, shaking time and type and concentration of surfactant) that could affect the performance of the method were evaluated. Total extraction of chloride from samples could be achieved when 1.0g of oil phase (0.5g of sample+0.5g of mineral oil) was emulsified in 5mL of a 2.5% (m/v) solution of Triton X-114. The obtained emulsion was shaken for 60min and broken by centrifugation for 5min at 5000rpm. The separated aqueous phase was collected, filtered and diluted before analysis by IC. Under these conditions, the limit of detection was 0.5μgg(-1) NaCl and the limit of quantification was 1.6μgg(-1) NaCl. We applied the method to the determination of chloride in six Brazilian crude oils and the results did not differ statistically from those obtained by the ASTM D6470 method when the paired Student-t-test, at 95% confidence level, was applied. Copyright © 2016 Elsevier B.V. All rights reserved.
Wiczkowski, Wieslaw; Romaszko, Ewa; Piskula, Mariusz K
The aim of this study was to investigate the bioavailability of anthocyanins from chokeberry juice with a dietary-relevant dose of anthocyanins. Thirteen healthy volunteers consumed chokeberry juice providing 0.8 mg of anthocyanins/kg of body weight. Before and after juice consumption, blood and urine were collected. Concentration of anthocyanins was measured with HPLC-PDA-MS-ESI. Cyanidin-3-galactoside comprised 66% of total chokeberry anthocyanins. Eight cyanidin derivatives were found in blood and urine after juice consumption. The maximum plasma anthocyanin concentration of 32.7 ± 2.9 nmol/L was reached at 1.3 ± 0.1 h after juice consumption. The anthocyanins' urine excretion rate (62.9 ± 5.0 nmol/h) was the highest within the first 2 h. In total, 0.25 ± 0.02% of the ingested anthocyanins was excreted by the renal route during 24 h, mainly as metabolites of cyanidin. According to these observations, after consumption of a dietary-relevant dose of anthocyanins as natural chokeberry juice, anthocyanins and their metabolites were present in plasma and urine of volunteers.
Toki, K; Saito, N; Shigihara, A; Honda, T
Three acylated anthocyanins were isolated from the scarlet flowers of Anemone coronaria 'St. Brigid Red' along with a known pigment, pelargonidin 3-lathyroside. The structures of the acylated pigments were based on a pelargonidin 3-lathyroside skeleton acylated at different positions with malonic acid. The first pigment was identified as pelargonidin 3-O-[2-(beta-D-xylopyranosyl)-6-O-(malonyl)-beta-D-galactopyranoside], the second was pelargonidin 3-O-[2-O-(beta-D-xylopyranosyl)-6-O-(methyl-malonyl)-beta-D-galactopyranoside], and the third was (6''-O-(pelargonidin 3-O-[2''-O-(beta-D-xylopyranosyl)-beta-D-galactopyranosyl]))((4-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-O-tartatryl)malonate.
Kalt, Wilhelmina; Liu, Yan; McDonald, Jane E; Vinqvist-Tymchuk, Melinda R; Fillmore, Sherry A E
LC-MS/MS revealed that metabolites of anthocyanins (Acn) were abundant in human urine (n = 17) even after 5 days with no dietary Acn. After intake of 250 mL of blueberry juice, parent Acn were 4% and Acn metabolites were 96% of the total urinary Acn for the following 24 h. Multiple reaction monitoring revealed 226 combinations of mass transition × retention times for known Acn and predicted Acn metabolites. These were dominated by aglycones, especially aglycone glucuronides. The diversity of Acn metabolites could include positional isomers of Acn conjugates and chalcones. The persistence of Acn metabolites suggested enterohepatic recycling leading to prolonged residence time. The prevalence of Acn metabolites based on pelargonidin, which is not present in blueberry juice, may reflect ongoing dehydroxylation and demethylation of other Acn via xenobiotic and colonic bacterial action. The results suggest that exposure to Acn-based flavonoid moieties is substantially greater than suggested by earlier research.
de Ferrars, R M; Czank, C; Zhang, Q; Botting, N P; Kroon, P A; Cassidy, A; Kay, C D
BACKGROUND AND PURPOSE Anthocyanins are phytochemicals with reported vasoactive bioactivity. However, given their instability at neutral pH, they are presumed to undergo significant degradation and subsequent biotransformation. The aim of the present study was to establish the pharmacokinetics of the metabolites of cyanidin-3-glucoside (C3G), a widely consumed dietary phytochemical with potential cardioprotective properties. EXPERIMENTAL APPROACH A 500 mg oral bolus dose of 6,8,10,3′,5′-13C5-C3G was fed to eight healthy male participants, followed by a 48 h collection (0, 0.5, 1, 2, 4, 6, 24, 48 h) of blood, urine and faecal samples. Samples were analysed by HPLC-ESI-MS/MS with elimination kinetics established using non-compartmental pharmacokinetic modelling. KEY RESULTS Seventeen 13C-labelled compounds were identified in the serum, including 13C5-C3G, its degradation products, protocatechuic acid (PCA) and phloroglucinaldehyde (PGA), 13 metabolites of PCA and 1 metabolite derived from PGA. The maximal concentrations of the phenolic metabolites (Cmax) ranged from 10 to 2000 nM, between 2 and 30 h (tmax) post-consumption, with half-lives of elimination observed between 0.5 and 96 h. The major phenolic metabolites identified were hippuric acid and ferulic acid, which peaked in the serum at approximately 16 and 8 h respectively. CONCLUSIONS AND IMPLICATIONS Anthocyanins are metabolized to a structurally diverse range of metabolites that exhibit dynamic kinetic profiles. Understanding the elimination kinetics of these metabolites is key to the design of future studies examining their utility in dietary interventions or as therapeutics for disease risk reduction. PMID:24602005
Li, Daotong; Wang, Pengpu; Luo, Yinghua; Zhao, Mengyao; Chen, Fang
Anthocyanins are one of the most widespread families of natural pigments in the plant kingdom. Their health beneficial effects have been documented in many in vivo and in vitro studies. This review summarizes the most recent literature regarding the health benefits of anthocyanins and their molecular mechanisms. It appears that several signaling pathways, including mitogen-activated protein kinase, nuclear factor κB, AMP-activated protein kinase, and Wnt/β-catenin, as well as some crucial cellular processes, such as cell cycle, apoptosis, autophagy, and biochemical metabolism, are involved in these beneficial effects and may provide potential therapeutic targets and strategies for the improvement of a wide range of diseases in future. In addition, specific anthocyanin metabolites contributing to the observed in vivo biological activities, structure-activity relationships as well as additive and synergistic efficacy of anthocyanins are also discussed.
Shoji, Toshihiko; Goda, Yukihiro; Toyoda, Masatake; Yanagida, Akio; Kanda, Tomomasa
Anthocyanin pigments, which are not found in apple juice, were detected in rosé cider. We confirmed by HPLC/DAD and LC/ESI-MS analyses that some of these anthocyanin pigments generated in rosé cider during vinification corresponded to those formed in model cider containing anthocyanin and flavan-3-ol in the presence of acetaldehyde. To confirm their structures, two anthocyanin pigments formed in a model cider containing cyanidin-3-galactoside and (-)-epicatechin in the presence of acetaldehyde were isolated and purified, and their structures were elucidated by high resolution FAB-MS and (1)H and (13)C NMR analyses. These two pigments were found to consist of cyanidin-3-galactoside and (-)-epicatechin linked by a CH(3)-CH bridge at the 8-position. They were diastereomers that differed in the configuration of the asymmetric methine carbon.
Bednár, Petr; Papousková, Barbora; Müller, Lukás; Barták, Petr; Stávek, Jan; Pavlousek, Pavel; Lemr, Karel
Hyphenation of capillary electrophoresis with electrospray ionization mass spectrometry was utilized for the monitoring of anthocyanins in wine and wine musts. CE/MS was performed in two electrolytes: 1) an acidic one (chloroacetate-ammonium, pH 2) and 2) a basic one with high selectivity towards derivatives containing vicinal hydroxy groups (borate-ammonium, pH 9). The setup of MS was optimized and the fragmentation of common anthocyanins was studied in detail. Attention was also focused on the fragmentation of anthocyanidin skeleton. The anthocyanidins substituted with hydroxy groups fragment via a cascade of neutral losses of water and carbon monoxide. Fragmentation of anthocyanidins containing a methoxy group on their B-ring starts with the cleavage of methane and/or methyl radical. The optimized method was utilized for the monitoring of changes in anthocyanin profile in red wines as well as the process of release of anthocyanins to wine must.
Potato phytonutrients include phenolic acids, flavonols, anthocyanins and carotenoids. Developmental effects on phytonutrient concentrations and gene expression was studied in white, yellow and purple potatoes. Purple potatoes contained the most total phenolics, which decreased during development (1...
Johnson, Mitch C.; Thomas, Andrew L.; Greenlief, C. Michael
The effects of frozen storage on the anthocyanin and polyphenol content of elderberry fruit juice are investigated. Juice from three genotypes of American elderberry (Adams II, Bob Gordon, and Wyldewood) was screened for total phenolic (TP) and total monomeric anthocyanin (TMA) content with spectrophotometric methods. The individual anthocyanin content (IAC) of the juice was tested by coupling solid phase extraction with ultra-performance liquid chromatography/tandem mass spectrometry. Juice samples were tested initially upon harvest, then again after 3, 6, and 9 months of frozen storage. Juice from the three different genotypes had significantly different TP, TMA, and IAC profiles initially (p<0.05). The TP,, TMA, and IAC content of the juice from different genotypes were significantly affected (p<0.05) by the frozen storage time, suggesting that both genotype and length of frozen storage time can affect the anthocyanin content of elderberry fruit juice. PMID:26028422
Duke, Stephen O.; Fox, Sue B.; Naylor, Aubrey W.
Results are reported which support the view that the photosynthetic photosystems are not involved in the high irradiance response (HIR) phenomenon of light-dependent anthocyanin biosynthesis in dark-grown Zea mays L. seedlings. A negative correlation between change in greening rates and change in light-dependent anthocyanin accumulation rates with age was demonstrated. Lack of chlorophyll synthesis in a strain of maize possessing a temperature-sensitive lesion for chlorophyll synthesis could not be correlated with light-induced anthocyanin accumulation. Furthermore, seedlings totally lacking photosynthetic capabilities, either due to a genetic lesion or to excision of all photosynthetic tissue, had an enhanced rate of photoinduced anthocyanin formation. This evidence indicates that the HIR results in the initiation of processes that are in competition with chloroplast development for substrate in normal, intact seedlings. PMID:16659449
Johnson, Mitch C; Thomas, Andrew L; Greenlief, C Michael
The effects of frozen storage on the anthocyanin and polyphenol content of elderberry fruit juice are investigated. Juice from three genotypes of American elderberry (Adams II, Bob Gordon, and Wyldewood) was screened for total phenolic (TP) and total monomeric anthocyanin (TMA) contents with spectrophotometric methods. The individual anthocyanin content (IAC) of the juice was tested by coupling solid phase extraction with ultraperformance liquid chromatography-tandem mass spectrometry. Juice samples were tested initially upon harvest and then again after 3, 6, and 9 months of frozen storage. Juice from the three different genotypes had significantly different TP, TMA, and IAC profiles initially (p < 0.05). The TP, TMA, and IAC contents of the juice from different genotypes were significantly affected (p < 0.05) by the frozen storage time, suggesting that both genotype and length of frozen storage time can affect the anthocyanin content of elderberry fruit juice.
Orzaez, Diego; Medina, Aurora; Torre, Sara; Fernández-Moreno, Josefina Patricia; Rambla, José Luis; Fernández-Del-Carmen, Asun; Butelli, Eugenio; Martin, Cathie; Granell, Antonio
Virus-induced gene silencing (VIGS) is a powerful tool for reverse genetics in tomato (Solanum lycopersicum). However, the irregular distribution of the effects of VIGS hampers the identification and quantification of nonvisual phenotypes. To overcome this limitation, a visually traceable VIGS system was developed for fruit, comprising two elements: (1) a transgenic tomato line (Del/Ros1) expressing Antirrhinum majus Delila and Rosea1 transcription factors under the control of the fruit-specific E8 promoter, showing a purple-fruited, anthocyanin-rich phenotype; and (2) a modified tobacco rattle virus VIGS vector incorporating partial Rosea1 and Delila sequences, which was shown to restore the red-fruited phenotype upon agroinjection in Del/Ros1 plants. Dissection of silenced areas for subsequent chemometric analysis successfully identified the relevant metabolites underlying gene function for three tomato genes, phytoene desaturase, TomloxC, and SlODO1, used for proof of concept. The C-6 aldehydes derived from lipid 13-hydroperoxidation were found to be the volatile compounds most severely affected by TomloxC silencing, whereas geranial and 6-methyl-5-hepten-2-one were identified as the volatiles most severely reduced by phytoene desaturase silencing in ripening fruit. In a third example, silencing of SlODO1, a tomato homolog of the ODORANT1 gene encoding a myb transcription factor, which regulates benzenoid metabolism in petunia (Petunia hybrida) flowers, resulted in a sharp accumulation of benzaldehyde in tomato fruit. Together, these results indicate that fruit VIGS, enhanced by anthocyanin monitoring, can be a powerful tool for reverse genetics in the study of the metabolic networks operating during fruit ripening.
Dia, Vermont P; Wang, Zhaoqin; West, Megan; Singh, Vijay; West, Leslie; de Mejia, Elvira Gonzalez
Anthocyanins are water-soluble pigments with health benefits and potential use as food colorants. The objectives of this work were to (1) determine optimum parameters for the extraction of anthocyanins from dried distillers grain with solubles (DDGS), (2) develop a method of anthocyanin extraction from DDGS, (3) quantify and identify the extracted anthocyanins, and (4) determine the effect of processing methods and corn cultivars on anthocyanin concentration. DDGS samples were prepared from purple (PC) and dark (DC) corn and processed using conventional enzymes (C) and granular starch hydrolyzing enzymes (GC). Three independent variables (ethanol concentration (0, 12.5, and 25%); liquid-to-solid ratio (30:1, 40:1, 50:1 mL/g); and extraction temperature (4, 22, and 40 °C)) and two dependent variables (anthocyanin concentration and a-value (redness)) were used. Results showed that dark corn DDGS gave anthocyanin concentration higher than that of purple corn. The GC process showed total anthocyanin concentration higher than that of the conventional method of DDGS production. The maximum anthocyanin concentration was obtained at 12.5% ethanol, 40:1 liquid-to-solid ratio, and 22 °C for C-PC [321.0 ± 37.3 μg cyanidin-3 glucoside (C3G) equivalent/g DDGS]. For GC-PC, 25% ethanol, 30:1 liquid-to-solid ratio, and 22 °C gave 741.4 ± 12.8 μg C3G equivalent/g DDGS. For GC-DC, 12.5% ethanol, 40:1 liquid-to-solid ratio, and 40 °C extraction gave 1573.4 ± 84.0 μg C3G equivalent/g DDGS. LC/MS-MS analysis showed that the major anthocyanins were cyanidin-3-glucoside, cyanidin-3-(6″-malonyl) glucoside, and peonidin-3-(6″malonyl) glucoside. In conclusion, anthocyanin extraction from colored corn DDGS can be optimized using 12.5% ethanol, 40:1 mL/g ratio, and 22 °C.
Hughes, Nicole M; Carpenter, Kaylyn L; Keidel, Timothy S; Miller, Charlene N; Waters, Matthew N; Smith, William K
Anthocyanins in upper (adaxial) leaf tissues provide greater photoprotection than in lower (abaxial) tissues, but also predispose tissues to increased shade acclimation and, consequently, reduced photosynthetic capacity. Abaxial anthocyanins may be a compromise between these costs/benefits. Plants adapted to shaded understory environments often exhibit red/purple anthocyanin pigmentation in lower (abaxial) leaf surfaces, but rarely in upper (adaxial) surfaces. The functional significance of this color pattern in leaves is poorly understood. Here, we test the hypothesis that abaxial anthocyanins protect leaves of understory plants from photo-oxidative stress via light attenuation during periodic exposure to high incident sunlight in the forest understory, without interfering with sunlight capture and photosynthesis during shade conditions. We utilize a cultivar of Colocasia esculenta exhibiting adaxial and abaxial anthocyanin variegation within individual leaves to compare tissues with the following color patterns: green adaxial, green abaxial (GG), green adaxial, red abaxial (GR), red adaxial, green abaxial (RG), and red adaxial, red abaxial (RR). Consistent with a photoprotective function of anthocyanins, tissues exhibited symptoms of increasing photoinhibition in the order (from least to greatest): RR, RG, GR, GG. Anthocyanic tissues also showed symptoms of shade acclimation (higher total chl, lower chl a/b) in the same relative order. Inconsistent with our hypothesis, we did not observe any differences in photosynthetic CO2 uptake under shade conditions between the tissue types. However, GG and GR had significantly (39 %) higher photosynthesis at saturating irradiance (A sat) than RG and RR. Because tissue types did not differ in nitrogen content, these patterns likely reflect differences in resource allocation at the tissue level, with greater nitrogen allocated toward energy processing in GG and GR, and energy capture in RG and RR (consistent with relative
Fang, Fang; Zhang, Xue-lian; Luo, Hong-hui; Zhou, Jia-jian; Gong, Yi-hui; Li, Wen-jun; Shi, Zhao-wan; He, Quan; Wu, Qing; Li, Lu; Jiang, Lin-lin; Cai, Zhi-gao; Oren-Shamir, Michal; Zhang, Zhao-qi; Pang, Xue-qun
In contrast to the detailed molecular knowledge available on anthocyanin synthesis, little is known about its catabolism in plants. Litchi (Litchi chinensis) fruit lose their attractive red color soon after harvest. The mechanism leading to quick degradation of anthocyanins in the pericarp is not well understood. An anthocyanin degradation enzyme (ADE) was purified to homogeneity by sequential column chromatography, using partially purified anthocyanins from litchi pericarp as a substrate. The purified ADE, of 116 kD by urea SDS-PAGE, was identified as a laccase (ADE/LAC). The full-length complementary DNA encoding ADE/LAC was obtained, and a polyclonal antibody raised against a deduced peptide of the gene recognized the ADE protein. The anthocyanin degradation function of the gene was confirmed by its transient expression in tobacco (Nicotiana benthamiana) leaves. The highest ADE/LAC transcript abundance was in the pericarp in comparison with other tissues, and was about 1,000-fold higher than the polyphenol oxidase gene in the pericarp. Epicatechin was found to be the favorable substrate for the ADE/LAC. The dependence of anthocyanin degradation by the enzyme on the presence of epicatechin suggests an ADE/LAC epicatechin-coupled oxidation model. This model was supported by a dramatic decrease in epicatechin content in the pericarp parallel to anthocyanin degradation. Immunogold labeling transmission electron microscopy suggested that ADE/LAC is located mainly in the vacuole, with essential phenolic substances. ADE/LAC vacuolar localization, high expression levels in the pericarp, and high epicatechin-dependent anthocyanin degradation support its central role in pigment breakdown during pericarp browning.
Takos, Adam M; Jaffé, Felix W; Jacob, Steele R; Bogs, Jochen; Robinson, Simon P; Walker, Amanda R
Anthocyanins are secondary metabolites found in higher plants that contribute to the colors of flowers and fruits. In apples (Malus domestica Borkh.), several steps of the anthocyanin pathway are coordinately regulated, suggesting control by common transcription factors. A gene encoding an R2R3 MYB transcription factor was isolated from apple (cv Cripps' Pink) and designated MdMYB1. Analysis of the deduced amino acid sequence suggests that this gene encodes an ortholog of anthocyanin regulators in other plants. The expression of MdMYB1 in both Arabidopsis (Arabidopsis thaliana) plants and cultured grape cells induced the ectopic synthesis of anthocyanin. In the grape (Vitis vinifera) cells MdMYB1 stimulated transcription from the promoters of two apple genes encoding anthocyanin biosynthetic enzymes. In ripening apple fruit the transcription of MdMYB1 was correlated with anthocyanin synthesis in red skin sectors of fruit. When dark-grown fruit were exposed to sunlight, MdMYB1 transcript levels increased over several days, correlating with anthocyanin synthesis in the skin. MdMYB1 gene transcripts were more abundant in red skin apple cultivars compared to non-red skin cultivars. Several polymorphisms were identified in the promoter of MdMYB1. A derived cleaved amplified polymorphic sequence marker designed to one of these polymorphisms segregated with the inheritance of skin color in progeny from a cross of an unnamed red skin selection (a sibling of Cripps' Pink) and the non-red skin cultivar Golden Delicious. We conclude that MdMYB1 coordinately regulates genes in the anthocyanin pathway and the expression level of this regulator is the genetic basis for apple skin color.
Cardoso, Silvana; Lau, Winston; Eiras Dias, José; Fevereiro, Pedro; Maniatis, Nikolas
Anthocyanin content is a trait of major interest in Vitis vinifera L. These compounds affect grape and wine quality, and have beneficial effects on human health. A candidate-gene approach was used to identify genetic variants associated with anthocyanin content in grape berries. A total of 445 polymorphisms were identified in 5 genes encoding transcription factors and 10 genes involved in either the biosynthetic pathway or transport of anthocyanins. A total of 124 SNPs were selected to examine association with a wide range of phenotypes based on RP-HPLC analysis and visual characterization. The phenotypes were total skin anthocyanin (TSA) concentration but also specific types of anthocyanins and relative abundance. The visual assessment was based on OIV (Organisation Internationale de la Vigne et du Vin) descriptors for berry and skin colour. The genes encoding the transcription factors MYB11, MYBCC and MYCB were significantly associated with TSA concentration. UFGT and MRP were associated with several different types of anthocyanins. Skin and pulp colour were associated with nine genes (MYB11, MYBCC, MYCB, UFGT, MRP, DFR, LDOX, CHI and GST). Pulp colour was associated with a similar group of 11 genes (MYB11, MYBCC, MYCB, MYCA, UFGT, MRP, GST, DFR, LDOX, CHI and CHSA). Statistical interactions were observed between SNPs within the transcription factors MYB11, MYBCC and MYCB. SNPs within LDOX interacted with MYB11 and MYCB, while SNPs within CHI interacted with MYB11 only. Together, these findings suggest the involvement of these genes in anthocyanin content and on the regulation of anthocyanin biosynthesis. This work forms a benchmark for replication and functional studies. PMID:23029369
Takos, Adam M.; Jaffé, Felix W.; Jacob, Steele R.; Bogs, Jochen; Robinson, Simon P.; Walker, Amanda R.
Anthocyanins are secondary metabolites found in higher plants that contribute to the colors of flowers and fruits. In apples (Malus domestica Borkh.), several steps of the anthocyanin pathway are coordinately regulated, suggesting control by common transcription factors. A gene encoding an R2R3 MYB transcription factor was isolated from apple (cv Cripps' Pink) and designated MdMYB1. Analysis of the deduced amino acid sequence suggests that this gene encodes an ortholog of anthocyanin regulators in other plants. The expression of MdMYB1 in both Arabidopsis (Arabidopsis thaliana) plants and cultured grape cells induced the ectopic synthesis of anthocyanin. In the grape (Vitis vinifera) cells MdMYB1 stimulated transcription from the promoters of two apple genes encoding anthocyanin biosynthetic enzymes. In ripening apple fruit the transcription of MdMYB1 was correlated with anthocyanin synthesis in red skin sectors of fruit. When dark-grown fruit were exposed to sunlight, MdMYB1 transcript levels increased over several days, correlating with anthocyanin synthesis in the skin. MdMYB1 gene transcripts were more abundant in red skin apple cultivars compared to non-red skin cultivars. Several polymorphisms were identified in the promoter of MdMYB1. A derived cleaved amplified polymorphic sequence marker designed to one of these polymorphisms segregated with the inheritance of skin color in progeny from a cross of an unnamed red skin selection (a sibling of Cripps' Pink) and the non-red skin cultivar Golden Delicious. We conclude that MdMYB1 coordinately regulates genes in the anthocyanin pathway and the expression level of this regulator is the genetic basis for apple skin color. PMID:17012405
Anthocyanins from fruit juices improve the antioxidant status of healthy young female volunteers without affecting anti-inflammatory parameters: results from the randomised, double-blind, placebo-controlled, cross-over ANTHONIA (ANTHOcyanins in Nutrition Investigation Alliance) study.
Kuntz, Sabine; Kunz, Clemens; Herrmann, Johannes; Borsch, Christian H; Abel, Georg; Fröhling, Bettina; Dietrich, Helmut; Rudloff, Silvia
Anthocyanins (ACN) can exert beneficial health effects not only through their antioxidative potential but also through modulation of inflammatory parameters that play a major role in CVD. A randomised cross-over study was carried out to investigate the effects of ACN-rich beverage ingestion on oxidation- and inflammation-related parameters in thirty healthy female volunteers. The participants consumed 330 ml of beverages (placebo, juice and smoothie with 8·9 (SD 0·3), 983·7 (SD 37) and 840·9 (SD 10) mg/l ACN, respectively) over 14 d. Before and after each intervention, blood and 24 h urine samples were collected. Plasma superoxide dismutase (SOD) and catalase activities increased significantly after ACN-rich beverage ingestion (P<0·001), whereas after placebo juice ingestion no increase could be observed. Plasma glutathione peroxidase and erythrocyte SOD activities were not affected. An increase in Trolox equivalent antioxidant capacity could also be observed after juice (P<0·001) and smoothie (P<0·01) ingestion. The plasma and urinary concentrations of malondialdehyde decreased after ACN-rich beverage ingestion (P<0·001), whereas those of 8-OH-2-deoxyguanosine as well as inflammation-related parameters (IL-2, -6, -8 and -10, C-reactive peptide, soluble cluster of differentiation 40 ligand, TNF-α, monocyte chemoattractant protein-1 and soluble cell adhesion molecules) were not affected. Thus, ingestion of ACN-rich beverages improves antioxidant enzyme activities and plasma antioxidant capacity, thus protecting the body against oxidative stress, a hallmark of ongoing atherosclerosis.
Wang, Hongxia; Fan, Weijuan; Li, Hong; Yang, Jun; Huang, Jirong; Zhang, Peng
Dihydroflavonol-4-reductase (DFR) is a key enzyme in the catalysis of the stereospecific reduction of dihydroflavonols to leucoanthocyanidins in anthocyanin biosynthesis. In the purple sweet potato (Ipomoea batatas Lam.) cv. Ayamurasaki, expression of the IbDFR gene was strongly associated with anthocyanin accumulation in leaves, stems and roots. Overexpression of the IbDFR in Arabidopsis tt3 mutants fully complemented the pigmentation phenotype of the seed coat, cotyledon and hypocotyl. Downregulation of IbDFR expression in transgenic sweet potato (DFRi) using an RNAi approach dramatically reduced anthocyanin accumulation in young leaves, stems and storage roots. In contrast, the increase of flavonols quercetin-3-O-hexose-hexoside and quercetin-3-O-glucoside in the leaves and roots of DFRi plants is significant. Therefore, the metabolic pathway channeled greater flavonol influx in the DFRi plants when their anthocyanin and proanthocyanidin accumulation were decreased. These plants also displayed reduced antioxidant capacity compared to the wild type. After 24 h of cold treatment and 2 h recovery, the wild-type plants were almost fully restored to the initial phenotype compared to the slower recovery of DFRi plants, in which the levels of electrolyte leakage and hydrogen peroxide accumulation were dramatically increased. These results provide direct evidence of anthocyanins function in the protection against oxidative stress in the sweet potato. The molecular characterization of the IbDFR gene in the sweet potato not only confirms its important roles in flavonoid metabolism but also supports the protective function of anthocyanins of enhanced scavenging of reactive oxygen radicals in plants under stressful conditions. PMID:24223813
Chung, Cheryl; Rojanasasithara, Thananunt; Mutilangi, William; McClements, David Julian
Anthocyanins are widely used as natural colorants in foods, but they are highly susceptible to chemical degradation during storage leading to color fading. This study examined the potential of natural quillaja saponin and polyphenols (vanillin, epigallocatechin gallate, green tea extract, and protocatechualdehyde) at inhibiting color fading of anthocyanins in model beverages. The purple carrot anthocyanin (0.025%) in model beverages (citric acid, pH 3.0) containing l-ascorbic acid (0.050%) degraded with a first-order reaction rate during storage (40°C/7days in light). The addition of polyphenols (0.2%) delayed color fading, with the most notable improvement observed with green tea extract addition. The half-life for anthocyanin color fading increased from 2.9 to 6.7days with green tea extract. Fluorescence quenching measurements showed that the green tea extract contained components that interacted with anthocyanins probably through hydrophobic interactions. Overall, this study provides valuable information about enhancing the stability of anthocyanins in beverage systems using polyphenols. Copyright © 2016 Elsevier Ltd. All rights reserved.
Tall, Jill M; Seeram, Navindra P; Zhao, Chengshui; Nair, Muraleedharan G; Meyer, Richard A; Raja, Srinivasa N
The use of complementary and alternative medicine (CAM) has increased in the United States and more patients are seeking CAM therapies for control of pain. The present investigation tested the efficacy of orally administered anthocyanins extracted from tart cherries on inflammation-induced pain behavior in rats. Paw withdrawal latency to radiant heat and paw withdrawal threshold to von Frey probes were measured. The first set of experiments examined the effects of tart cherry anthocyanins (400 mg/kg) on the nociceptive behaviors and edema associated with inflammation induced by intraplantar injection of 1% carrageenan. These studies also included tests of motor coordination. The second set of experiments determined if tart cherry anthocyanins (15, 85, and 400 mg/kg) dose-dependently affected the inflammation induced by intraplantar injection of 25% complete Freund's adjuvant. We found that tart cherry extracts reduce inflammation-induced thermal hyperalgesia, mechanical hyperalgesia and paw edema. The suppression of thermal hyperalgesia was dose-dependent and the efficacy of highest dose (400 mg/kg) was similar to indomethacin (5 mg/kg). The highest dose anthocyanin (400 mg/kg) had no effects on motor function. These data suggest that tart cherry anthocyanins may have a beneficial role in the treatment of inflammatory pain. The antihyperalgesic effects may be related to the anti-inflammatory and antioxidant properties of anthocyanins. A better understanding of the modulatory role of dietary constituents and phytonutrients on pain will offer further therapeutic options for treating patients with persistent and chronic pain conditions.
Chung, Cheryl; Rojanasasithara, Thananunt; Mutilangi, William; McClements, David Julian
This study investigated the potential of gum arabic to improve the stability of anthocyanins that are used in commercial beverages as natural colourants. The degradation of purple carrot anthocyanin in model beverage systems (pH 3.0) containing L-ascorbic acid proceeded with a first-order reaction rate during storage (40 °C for 5 days in light). The addition of gum arabic (0.05-5.0%) significantly enhanced the colour stability of anthocyanin, with the most stable systems observed at intermediate levels (1.5%). A further increase in concentration (>1.5%) reduced its efficacy due to a change in the conformation of the gum arabic molecules that hindered their exposure to the anthocyanins. Fluorescence quenching measurements showed that the anthocyanin could have interacted with the glycoprotein fractions of the gum arabic through hydrogen bonding, resulting in enhanced stability. Overall, this study provides valuable information about enhancing the stability of anthocyanins in beverage systems using natural ingredients.
Howard, Luke R; Brownmiller, Cindi; Prior, Ronald L; Mauromoustakos, Andy
Chokeberry anthocyanins are susceptible to degradation during processing and storage of processed products. This study determined the effects of three pH levels (2.8, 3.2, and 3.6) and four β-cyclodextrin (BCD) concentrations (0, 0.5, 1, and 3%) alone and in combination on the stability of chokeberry juice anthocyanins before and after pasteurization and over 8 months of storage at 4 and 25 °C. Lowering the pH from 3.6 to 2.8 in the absence of BCD provided marginal protection against anthocyanin losses during processing and storage. Addition of 3% BCD at the natural chokeberry pH of 3.6 resulted in excellent protection of anthocyanins, with 81 and 95% retentions after 8 months of storage at 25 and 4 °C, respectively. The protective effect of BCD was lessened with concentrations <3% and reduction in pH, indicating changes in anthocyanin structure play an important role in BCD stabilization of anthocyanins.
Hornedo-Ortega, Ruth; Álvarez-Fernández, M Antonia; Cerezo, Ana B; Garcia-Garcia, Isidoro; Troncoso, Ana M; Garcia-Parrilla, M Carmen
Anthocyanins are the major polyphenolic compounds in strawberry fruit responsible for its color. Due to their sensitivity, they are affected by food processing techniques such as fermentation that alters both their chemical composition and organoleptic properties. This work aims to evaluate the impact of different fermentation processes on individual anthocyanins compounds in strawberry wine and vinegar by UHPLC-MS/MS Q Exactive analysis. Nineteen, 18, and 14 anthocyanin compounds were identified in the strawberry initial substrate, strawberry wine, and strawberry vinegar, respectively. Four and 8 anthocyanin compounds were tentatively identified with high accuracy for the 1st time to be present in the beverages obtained by alcoholic fermentation and acetic fermentation of strawberry, respectively. Both, the total and the individual anthocyanin concentrations were decreased by both fermentation processes, affecting the alcoholic fermentation to a lesser extent (19%) than the acetic fermentation (91%). Indeed, several changes in color parameters have been assessed. The color of the wine and the vinegar made from strawberry changed during the fermentation process, varying from red to orange color, this fact is directly correlated with the decrease of anthocyanins compounds. © 2017 Institute of Food Technologists®.
Gould, Kevin S.; Dudle, Dana A.; Neufeld, Howard S.
Red-stemmed plants are extremely common, yet the functions of cauline anthocyanins are largely unknown. The possibility that photoabatement by anthocyanins in the periderm reduces the propensity for photoinhibition in cortical chlorenchyma was tested for Cornus stolonifera. Anthocyanins were induced in green stems exposed to full sunlight. PSII quantum yields (ФPSII) and photochemical quenching coefficients were depressed less in red than in green stems, both under a light ramp and after prolonged exposures to saturating white light. These differences were primarily attributable to the attenuation of PAR, especially green/yellow light, by anthocyanins. However, the red internodes also had less chlorophyll and higher carotenoid:chlorophyll ratios than the green, and when the anthocyanic periderm was removed, small differences in the ФPSII of the underlying chlorenchyma were retained. Thus, light screening by cauline anthocyanins is important, but is only part of a set of protective acclimations to high irradiance. Hourly measurements of ФPSII on established trees under natural daylight indicated a possible advantage of red versus green stems under sub-saturating diffuse, but not direct sunlight. To judge the wider applicability of the hypothesis, responses to high light were compared for red and green stems across five further unrelated species. There was a strong, linear, interspecific correlation between photoprotective advantage and anthocyanin concentration differences among red and green internodes. The photoprotective effect appears to be a widespread phenomenon. PMID:20400528
Wang, Zhong-Wei; Jiang, Cong; Wen, Qiang; Wang, Na; Tao, Yuan-Yuan; Xu, Li-An
Camellia chekiangoleosa is an important species of genus Camellia. It provides high-quality edible oil and has great ornamental value. The flowers are big and red which bloom between February and March. Flower pigmentation is closely related to the accumulation of anthocyanin. Although anthocyanin biosynthesis has been studied extensively in herbaceous plants, little molecular information on the anthocyanin biosynthesis pathway of C. chekiangoleosa is yet known. In the present study, a cDNA library was constructed to obtain detailed and general data from the flowers of C. chekiangoleosa. To explore the transcriptome of C. chekiangoleosa and investigate genes involved in anthocyanin biosynthesis, a 454 GS FLX Titanium platform was used to generate an EST dataset. About 46,279 sequences were obtained, and 24,593 (53.1%) were annotated. Using Blast search against the AGRIS, 1740 unigenes were found homologous to 599 Arabidopsis transcription factor genes. Based on the transcriptome dataset, nine anthocyanin biosynthesis pathway genes (PAL, CHS1, CHS2, CHS3, CHI, F3H, DFR, ANS, and UFGT) were identified and cloned. The spatio-temporal expression patterns of these genes were also analyzed using quantitative real-time polymerase chain reaction. The study results not only enrich the gene resource but also provide valuable information for further studies concerning anthocyanin biosynthesis.
Huang, Xiaojie; Li, Jing; Shang, Hongli; Meng, Xin
The effects of postharvest methyl jasmonate (MeJA) fumigation on total soluble solids (TSS), titratable acidity (TA), ascorbic acid, total phenolic content (TPC), total monomeric anthocyanins (TMAs), individual anthocyanins and antioxidant activity of blueberries stored at 1 °C for 28 days were evaluated. Prior to storage, the blueberries were fumigated with 0.05 mmol L(-1) MeJA for 12 h. Control blueberries were subjected to the same conditions but were not exposed to MeJA. MeJA treatment had no adverse effect on TSS and TA and inhibited the decrease in ascorbic acid during storage. MeJA treatment induced an enhancement in TPC on day 21; TPC decreased thereafter. Similarly, a significant increase in TMAs and individual anthocyanins was observed 21 days after MeJA treatment. TPC, TMAs and individual anthocyanins increased in control fruits on day 7 and decreased thereafter. Moreover, MeJA treatment maintained higher levels of antioxidant activity during the entire storage period. These results suggest that cold storage enhances TPC, TMAs and individual anthocyanin content during short-term storage. However, postharvest application of MeJA to blueberries enhances TPC, TMAs and individual anthocyanin content during long-term storage. © 2014 Society of Chemical Industry.
Psittacofulvins represent an unusual class of pigments (noncarotenoid lipochromes), which are found only in the red, orange, and yellow plumage of parrots. Anthocyanins are flavonoids, and they are one of the primary types of colorants found in plants. Blue butterflies acquire blue and UV hues on their wings, owing to the presence of flavonoids. It is assumed that these natural pigments are valuable antioxidants because they are able to scavenge free radicals. The aim of this investigation is to rationalize the scavenging activity of psittacofulvins and anthocyanins, in terms of the one electron transfer mechanism, taking into account that to prevent oxidative stress, substances must either donate or accept electrons. Density functional approximation calculations are used to obtain ionization potentials, electron affinities, electrodonating, and electroaccepting power indexes. Taking these values, a donator acceptor map (DAM) was constructed, indicating that anthocyanins are good electron donors, whereas psittacofulvins are good electron acceptors. Anthocyanins and vitamins are antioxidants, whereas psittacofulvins and carotenoids are antireductants (oxidants). In terms of solvent effects, animal pigments (carotenoids, psittacofulvins, and anthocyanins) are much better electron acceptors in water than in either the gas phase or benzene. Solvent effects do not alter the electron donor capacity of vitamins, but anthocyanins become effective electron acceptors in water, rather than effective electron donors. The information presented here may also be valuable for the design and analysis of further experiments.
Borghesi, Eva; González-Miret, M Lourdes; Escudero-Gilete, M Luisa; Malorgio, Fernando; Heredia, Francisco J; Meléndez-Martínez, Antonio J
One nonanthocyanin-accumulating (Ailsa Craig) and three anthocyanin-accumulating tomato genotypes (Anthocyanin fruit type, Atroviolaceum, and Sun Black) were analyzed to assess differences in their carotenoid and anthocyanin levels and color and to evaluate the effects of nutrient solutions with different salt concentrations on these parameters. The carotenoid content of control Atroviolaceum tomatoes was ca. 2-2.5-fold higher relative to the other two types, and the color of its puree could be visually distinguished from those of other genotypes. Salinity stress led in some cases to a 2-3-fold increase in the lycopene content. Saline treatment increased the accumulation of total anthocyanins in fruits of Sun Black (2-fold increase), while it reduced it in fruits of Anthocyanin (10-fold decrease). In general, the treatment increased the differences in color of different purees. These results indicate that salinity stress can lead to similar or higher increases in tomato carotenoids than those achieved by genetic engineering. In addition, these changes were accompanied by visually discernible color differences in tomato products. Our findings show the considerable potential of exploiting saline soils to obtain tomatoes with higher levels of secondary metabolites like carotenoids and anthocyanins.
do Carmo Brito, Brenda de Nazaré; da Silva Pena, Rosinelson; Santos Lopes, Alessandra; Campos Chisté, Renan
Jambolão fruits are promising sources of anthocyanins, and in this study, the jambolão fruit from the Brazilian Amazonian region was characterized and the efficiency of six ethanol-based solutions to extract anthocyanins was determined. Moreover, the color changes of anthocyanin extracts, as influenced by different pH conditions (pH from 1.0 to 8.0), were evaluated. The fruits exhibited high contents of total anthocyanins (296 mg/100 g) and the CIELAB parameters characterized jambolão as a purple-red colored fruit (a(*) = 20.30, b(*) = -4.17, and hab∘= 348.39). Among the six different ethanol-based solutions, ethanol 95% with 1% of HCl (v/v) was the most efficient solution to extract anthocyanins from jambolão fruits. Furthermore, the CIELAB parameters were characterized as useful tool to monitor the color changes of anthocyanins of jambolão over the tested pH range. Therefore, jambolão fruits from Amazonian region have technological potential for the application by food, pharmaceutical, and cosmetic industries. © 2017 Institute of Food Technologists®.
de Villiers, André; Cabooter, Deirdre; Lynen, Frédéric; Desmet, Gert; Sandra, Pat
The analysis of anthocyanins in natural products is of significant relevance in recent times due to the recognised health benefits associated with their consumption. In red grapes and wines in particular, anthocyanins are known to contribute important properties to the sensory (colour and taste), anti-oxidant- and ageing characteristics. However, the detailed investigation of the alteration of these compounds during wine ageing is hampered by the challenges associated with the separation of grape-derived anthocyanins and their derived products. High performance liquid chromatography (HPLC) is primarily used for this purpose, often in combination with mass spectrometric (MS) detection, although conventional HPLC methods provide incomplete resolution. We have previously demonstrated how on-column inter-conversion reactions are responsible for poor chromatographic efficiency in the HPLC analysis of anthocyanins, and how an increase in temperature and decrease in particle size may improve the chromatographic performance. In the current contribution an experimental configuration for the high efficiency analysis of anthocyanins is derived using the kinetic plot method (KPM). Further, it is shown how analysis under optimal conditions, in combination with MS detection, delivers much improved separation and identification of red wine anthocyanins and their derived products. This improved analytical performance holds promise for the in-depth investigation of these influential compounds in wine during ageing. Copyright © 2011 Elsevier B.V. All rights reserved.
Shoji, T; Yanagida, A; Kanda, T
Anthocyanin pigments from rosé cider and red wine, which is a sparkling wine made from apples, were separated by gel permeation chromatography (GPC) using a TSK-GEL Toyopearl HW-40 (F) column with a 6:4 mixture of acetone and 8 M urea (pH 2.0) as the eluent. Under this condition, all phenolic compounds containing monomeric anthocyanins (mainly, cyanidin-3-galactoside; Cyn-3-gal), oligomeric and polymeric anthocyanins, chlorogenic acid, catechin, epicatechin, procyanidin B2 (PB2), and procyanidin C1 (PC1) in the apples and rosé cider were found to elute according to molecular weight. Bleaching of the anthocyanin pigments by SO(2) was gradually effective in the fractions separated by GPC according to elution volume. In the case of rosé cider, the levels of Cyn-3-gal decreased markedly during fermentation and then decreased gradually during maturation. We confirmed that anthocyanin polymers are not detectable in apple juice; these polymers are produced during fermentation and maturation as determined by GPC. The polymeric anthocyanins from red wine could be separated by this method, too.
Choung, M G; Baek, I Y; Kang, S T; Han, W Y; Shin, D C; Moon, H P; Kang, K H
Anthocyanin pigments in seed coats of black soybean (Glycine max (L.) Merr.) were extracted with 1% HCl-CH(3)OH, and the crude anthocyanin extract was purified by Shepadex LH-20 and Lichroprep RP-18 open-column chromatography. Three major anthocyanins were isolated, and their chemical structures were identified by spectroscopic methods (UV-visible, FABMS, (1)H and (13)C NMR, and by TLC). The complete structures of these anthocyanins were elucidated as delphinidin-3-glucoside, cyanidin-3-glucoside, and petunidin-3-glucoside. Among them, petunidin-3-glucoside was identified as a new anthocyanin in black soybeans. On the basis of RP-HPLC with a UV-vis detector, the contents of delphinidin-3-glucoside, cyanidin-3-glucoside, petunidin-3-glucoside, and total anthocyanins in seed coats of 10 black soybeans were found in the ranges of 0-3.71, 0.94-15.98, 0-1.41, and 1.58-20.18 mg/g, respectively. The results obtained in this study imply that the seed coats of black soybean can be used as a good source for cyanidin-3-glucoside and delphinidin-3-glucoside.
Moldovan, Bianca; David, Luminiţa
Cornelian cherry (Cornus mas L.) fruits are known for their significant amounts of anthocyanins which can be used as natural food colorants. The storage stability of anthocyanins from these fruit extracts, at different temperatures (2 °C, 25 °C and 75 °C), pH 3.02, in the presence of two of the most widely employed food preserving agents (sodium benzoate and potassium sorbate) was investigated. The highest stability was exhibited by the anthocyanin extract stored at 2 °C without any added preservative, with half-life and constant rate values of 1443.8 h and 0.48 × 10(-3) h(-1), respectively. The highest value of the degradation rate constant (82.76 × 10(-3)/h) was obtained in the case of anthocyanin extract stored at 75 °C without any added preservative. Experimental results indicate that the storage degradation of anthocyanins followed first-order reaction kinetics under each of the investigated conditions. In aqueous solution, the food preservatives used were found to have a slight influence on the anthocyanins' stability.
Yamazaki, Mami; Nakajima, Jun-ichiro; Yamanashi, Mutsuki; Sugiyama, Mitsuyo; Makita, Yukiko; Springob, Karin; Awazuhara, Motoko; Saito, Kazuki
We have investigated metabolite profiles and gene expression in two chemo-varietal forms, red and green forms, of Perilla frutescens var. crispa. Striking difference in anthocyanin content was observed between the red and green forms. Anthocyanin, mainly malonylshisonin, was highly accumulated in the leaves of the red form but not in the green form. Less obvious differences were also observed in the stems. However, there was no remarkable difference in the contents and patterns of flavones and primary metabolites such as inorganic anions, organic anions and amino acids. These results suggest that only the regulation of anthocyanin production, but not that of other metabolites, differs in red and green forms. Microscopic observation and immunohistochemical studies indicated that the epidermal cells of leaves and stems are the sites of accumulation of anthocyanins and localization of anthocyanidin synthase protein. By differential display of mRNA from the leaves of red and green forms, we could identify several genes encoding anthocyanin-biosynthetic enzymes and presumptive regulatory proteins. The possible regulatory network leading to differential anthocyanin accumulation in a form-specific manner is discussed.
Du, Hui; Wu, Jie; Ji, Kui-Xian; Zeng, Qing-Yin; Bhuiya, Mohammad-Wadud; Su, Shang; Shu, Qing-Yan; Ren, Hong-Xu; Liu, Zheng-An; Wang, Liang-Sheng
Anthocyanins are major pigments in plants. Methylation plays a role in the diversity and stability of anthocyanins. However, the contribution of anthocyanin methylation to flower coloration is still unclear. We identified two homologous anthocyanin O-methyltransferase (AOMT) genes from purple-flowered (PsAOMT) and red-flowered (PtAOMT) Paeonia plants, and we performed functional analyses of the two genes in vitro and in vivo. The critical amino acids for AOMT catalytic activity were studied by site-directed mutagenesis. We showed that the recombinant proteins, PsAOMT and PtAOMT, had identical substrate preferences towards anthocyanins. The methylation activity of PsAOMT was 60 times higher than that of PtAOMT in vitro. Interestingly, this vast difference in catalytic activity appeared to result from a single amino acid residue substitution at position 87 (arginine to leucine). There were significant differences between the 35S::PsAOMT transgenic tobacco and control flowers in relation to their chromatic parameters, which further confirmed the function of PsAOMT in vivo. The expression levels of the two homologous AOMT genes were consistent with anthocyanin accumulation in petals. We conclude that AOMTs are responsible for the methylation of cyanidin glycosides in Paeonia plants and play an important role in purple coloration in Paeonia spp. PMID:26208646
Misyura, Maksym; Colasanti, Joseph; Rothstein, Steven J
Anthocyanin production is a characteristic response of flowering plants to unfavourable environmental conditions. The potential roles of flavonoids and anthocyanins in plant growth were investigated by growing Arabidopsis thaliana anthocyanin production mutants (transparent testa) under limiting nitrogen and high light conditions. Inability to produce kaempferol or subsequent intermediate compounds by some transparent testa lines was correlated with less biomass accumulation in mature plants compared with wild-type control plants under all growth conditions tested. However, under both limiting nitrogen and high light chronic stress conditions, mutant lines defective in later steps of the anthocyanin production pathway produced the same or more biomass than wild-type plants. No difference in senescence between transparent testa and wild-type plants was found using chlorophyll catabolism and SAG12 expression measurements, and no mutants were impaired in the ability to remobilize nutrients from the vegetative to reproductive tissues. Moreover, the absence of anthocyanin and/or upstream flavonoids does not affect the ability of plants to respond to limiting nitrogen by reducing photosynthetic capacity. These results support a role for kaempferol and quercetin accumulation in normal plant growth and development. Further, the absence of anthocyanins has no effect on plant growth under the chronic stress conditions tested.
Rossi, Antonietta; Serraino, Ivana; Dugo, Paola; Di Paola, Rosanna; Mondello, Luigi; Genovese, Tiziana; Morabito, Domenica; Dugo, Giovanni; Sautebin, Lidia; Caputi, Achille P; Cuzzocrea, Salvatore
Anthocyanins are a group of naturally occuring phenolic compounds related to the coloring of plants, flowers and fruits. These pigments are important as quality indicators, as chemotaxonomic markers and for their antioxidant activities. Here, we have investigated the therapeutic efficacy of anthocyanins contained in blackberry extract (cyanidin-3-O-glucoside represents about 80% of the total anthocyanin contents) in an experimental model of lung inflammation induced by carrageenan in rats. Injection of carrageenan into the pleural cavity elicited an acute inflammatory response characterized by fluid accumulation which contained a large number of neutrophils as well as an infiltration of polymorphonuclear leukocytes in lung tissues and subsequent lipid peroxidation, and increased production of nitrite/nitrate (NOx) and prostaglandin E2 (PGE2). All parameters of inflammation were attenuated in a dose-dependent manner by anthocyanins (10, 30 mg kg(-1) 30 min before carrageenan). Furthermore, carrageenan induced an upregulation of the adhesion molecule ICAM-1, nitrotyrosine and poly (ADP-ribose) synthetase (PARS) as determined by immunohistochemical analysis of lung tissues. The degree of staining was lowered by anthocyanins treatment. Thus, the anthocyanins contained in the blackberry extract exert multiple protective effects in carrageenan-induced pleurisy.
Su, Nana; Wu, Qi; Cui, Jin
Effects of nitrogen (N) deficiency and sucrose (Suc) addition on regulation of anthocyanin biosynthesis and their relationship were investigated in this study. Radish sprouts subjected to N deficiency had 50% higher anthocyanin accumulation than when grown in Hoagland solution (a nutrient medium with all macronutrients). The contents of endogenous soluble sugars (Suc, fructose, and glucose) in the hypocotyls were also markedly increased by N limitation, with Suc showing the highest increase. Inhibition of carbohydrate biosynthesis by addition of 3-(3,4-dichlorophenyl)-1,1-dimethylurea (DCMU) also eliminated N deficiency-induced anthocyanin accumulation. The latter was further supported by the expression of anthocyanin biosynthesis related genes and decreased activities of nitrate reductase in the presence of Suc. Together our results indicate that N deficiency-induced anthocyanin accumulation was, at least partly, dependent on the increase of the soluble sugar, especially Suc. This work is the first comprehensive study on relationship between N deficiency and sugar content on anthocyanin accumulation in the hypocotyls of radish sprouts. PMID:28083009
Septiani, N. L. W.; Yuliarto, B.; Iqbal, M.; Nugraha
Zinc Oxide nanoparticles have been successfully synthesized by utilizing anthocyanin as a capping agent by thermal decomposition of precursor route. The influence of the high and low concentrations of the anthocyanin to the shape and size of ZnO was investigated in this work. The anthocyanin was obtained from Indonesia black rice extract with methanol as a solvent. The crystallinity and morphology properties were characterized by X-Ray Diffractometer (XRD), and Scanning Electron Microscope (SEM), respectively. XRD result showed that ZnO was formed with good crystallinity without any second phase and had a hexagonal wurtzite crystal structure. SEM result revealed that ZnO with a low concentration of anthocyanin has a spherical shape with a uniform size of about 16 nm while ZnO with a high concentration of anthocyanin has a rod-like shape. The size of spherical ZnO in this work is smaller than ZnO from the same method of synthesis without anthocyanin (~30 nm).
Fan, Zi-Luan; Wang, Zhen-Yu; Zuo, Li-Li; Tian, Shuang-Qi
There is a growing concern about the serious harm of radioactive materials, which are widely used in energy production, scientific research, medicine, industry and other areas. In recent years, owing to the great side effects of anti-radiation drugs, research on the radiation protectants has gradually expanded from the previous chemicals to the use of natural anti-radiation drugs and functional foods. Some reports have confirmed that anthocyanins are good antioxidants, which can effectively eliminate free radicals, but studies on the immunoregulatory and anti-radiation effects of anthocyanins from lingonberry (ALB) are less reported. In this experiment, mice were given orally once daily for 14 consecutive days before exposure to 6 Gy of gamma-radiation and were sacrificed on the 7th day post-irradiation. The results showed that the selected dose of extract did not lead to acute toxicity in mice; while groups given anthocyanins orally were significantly better than radiation control group according to blood analysis; pretreatment of anthocyanins significantly (p < 0.05) enhanced the thymus and spleen indices and spleen cell survival compared to the irradiation control group. Pretreatment with anthocyanins before irradiation significantly reduced the numbers of micronuclei (MN) in bone marrow polychromatic erythrocytes (PCEs). These findings indicate that anthocyanins have immunostimulatory potential against immunosuppression induced by the radiation. PMID:23249859
Rothstein, Steven J.
Anthocyanin production is a characteristic response of flowering plants to unfavourable environmental conditions. The potential roles of flavonoids and anthocyanins in plant growth were investigated by growing Arabidopsis thaliana anthocyanin production mutants (transparent testa) under limiting nitrogen and high light conditions. Inability to produce kaempferol or subsequent intermediate compounds by some transparent testa lines was correlated with less biomass accumulation in mature plants compared with wild-type control plants under all growth conditions tested. However, under both limiting nitrogen and high light chronic stress conditions, mutant lines defective in later steps of the anthocyanin production pathway produced the same or more biomass than wild-type plants. No difference in senescence between transparent testa and wild-type plants was found using chlorophyll catabolism and SAG12 expression measurements, and no mutants were impaired in the ability to remobilize nutrients from the vegetative to reproductive tissues. Moreover, the absence of anthocyanin and/or upstream flavonoids does not affect the ability of plants to respond to limiting nitrogen by reducing photosynthetic capacity. These results support a role for kaempferol and quercetin accumulation in normal plant growth and development. Further, the absence of anthocyanins has no effect on plant growth under the chronic stress conditions tested. PMID:23162120
Qu, Jun-Ge; Zhang, Wei; Jin, Mei-Fang; Yu, Xing-Ju
The instability of secondary metabolite production is a ubiquitous problem in plant cell culture. To understand the instability, the investigation of anthocyanin accumulation in suspension cultures of Vitis vinifera, as a model system, has been initiated in our laboratory. Suspension culture of a relatively homogeneous cell line E of V. vinifera, was established by long-term cell line selection by anthocyanin content differentiation. The aggregate size of E was smaller than that of other cell lines obtained by routine screening method. The variation coefficients of anthocyanin content in suspension cultures of E were 8.7% in long-term subcultures and 5% in repeated flasks, respectively. The effects of elicitor, precursor feeding and light irridiation on biomass and anthocyanin accumulation in suspension cultures of E had been investigated and the results showed that all the variation coefficients were lower than 12% and this indicated the importance of homogeneity on stable production in plant cell culture. With the combination treatment of 30micromol/L phenylalanine and 218micromol/L methyl jasmonate in the dark in suspension cultures of E, the anthocyanin content and production in suspension culture of E was 5.89-fold and 4.30-fold of the controls, respectively, and all the variation coefficients of biomass and anthocyanin accumulation were lower than those of the controls in 5 successive subcultures.
Lim, Soyoung; Xu, Jianteng; Kim, Jaeyong; Chen, Tzu-Yu; Su, Xiaoyu; Standard, Joseph; Carey, Edward; Griffin, Jason; Herndon, Betty; Katz, Benjamin; Tomich, John; Wang, Weiqun
Scope Anthocyanins, the natural pigments in plant foods, have been associated with cancer prevention. However, the content of anthocyanins in staple foods is typically low and the mechanisms by which they exert anti-cancer activity is not yet fully defined. Methods and results We selected an anthocyanin-enriched purple-fleshed sweet potato clone, P40, and investigated its potential anti-cancer effect in both in vitro cell culture and in vivo animal model. In addition to a high level of total phenolics and antioxidant capacity, P40 possesses a high content of anthocyanins at 7.5 mg/g dry matter. Treatment of human colonic SW480 cancer cells with P40 anthocyanin extracts at 0–40 μM of peonidin-3-glucoside equivalent resulted in a dose-dependent decrease in cell number due to cytostatic arrest of cell cycle at G1 phase but not cytotoxicity. Furthermore, dietary P40 at 10–30% significantly suppressed azoxymethane-induced formation of aberrant crypt foci in the colons of CF-1 mice in conjunction with, at least in part, a lesser proliferative PCNA and a greater apoptotic caspase-3 expression in the colon mucosal epithelial cells. Conclusion These observations, coupled with both in vitro and in vivo studies reported here, suggest anthocyanin-enriched sweet potato P40 may protect against colorectal cancer by inducing cell cycle arrest, anti-proliferative and apoptotic mechanisms. PMID:23784800
Sun, Yi; Li, Hong; Huang, Ji-Rong
Anthocyanins are synthesized in the cytosolic surface of the endoplasmic reticulum (ER) but dominantly accumulate in the vacuole. Little is known about how anthocyanins are transported from the ER to the vacuole. Here, we provide evidence supporting that Transparent Testa 19 (TT19), a glutathione S-transferase (GST), functions as a carrier to transport cyanidin and/or anthocyanins to the tonoplast. We identified a novel tt19 mutant (tt19-7), which barely accumulates anthocyanins but produces a 36% higher level of flavonol than the wild-type (WT), from ethyl methanesulfonate mutagenized seeds. Expressing TT19-fused green fluorescence protein (GFP) in tt19-7 rescues the mutant phenotype in defective anthocyanin biosynthesis, indicating that TT19-GFP is functional. We further showed that TT19-GFP is localized not only in the cytoplasm and nuclei, but also on the tonoplast. The membrane localization of TT19-GFP was further ascertained by immunoblot analysis. In vitro assay showed that the purified recombinant TT19 increases water solubility of cyanidin (Cya) and cyanidin-3-O-glycoside (C3G). Compared with C3G, Cya can dramatically quench the intrinsic tryptophan fluorescence of TT19 to much lower levels, indicating a higher affinity of TT19 to Cya than to C3G. Isothermal titration calorimetry analysis also confirmed physical interaction between TT19 and C3G. Taken together, our data reveal molecular mechanism underlying TT19-mediated anthocyanin transportation.
Qian, Bing-Jun; Liu, Jian-Hua; Zhao, Shu-Juan; Cai, Jian-Xiong; Jing, Pu
The mechanism by which copigments stabilize colour, by protecting anthocyanin chromophores from nucleophilic attack, seems well accepted. This study was to determine effects of gallic/ferulic/caffeic acids on colour intensification and anthocyanin stability. Molecular dynamics simulations were applied to explore molecular interactions. Phenolic acids intensified the colour by 19%∼27%. Colour fading during heating followed first-order reactions with half-lives of 3.66, 9.64, 3.50, and 3.39h, whereas anthocyanin degradation, determined by the pH differential method (or HPLC-PDA), followed second-order reactions with half-lives of 3.29 (3.40), 3.43 (3.39), 2.29 (0.39), and 2.72 (0.32)h alone or with gallic/ferulic/caffeic acids, respectively, suggesting that anthocyanin degradation was faster than the colour fading. The strongest protection of gallic acids might be attributed to the shortest distance (4.37Å) of its aromatic ring to the anthocyanin (AC) panel. Hyperchromic effects induced by phenolic acids were pronounced and they obscured the accelerated anthocyanin degradation due to self-association interruption. Copyright © 2017 Elsevier Ltd. All rights reserved.
Fan, Zi-Luan; Wang, Zhen-Yu; Zuo, Li-Li; Tian, Shuang-Qi
There is a growing concern about the serious harm of radioactive materials, which are widely used in energy production, scientific research, medicine, industry and other areas. In recent years, owing to the great side effects of anti-radiation drugs, research on the radiation protectants has gradually expanded from the previous chemicals to the use of natural anti-radiation drugs and functional foods. Some reports have confirmed that anthocyanins are good antioxidants, which can effectively eliminate free radicals, but studies on the immunoregulatory and anti-radiation effects of anthocyanins from lingonberry (ALB) are less reported. In this experiment, mice were given orally once daily for 14 consecutive days before exposure to 6 Gy of gamma-radiation and were sacrificed on the 7th day post-irradiation. The results showed that the selected dose of extract did not lead to acute toxicity in mice; while groups given anthocyanins orally were significantly better than radiation control group according to blood analysis; pretreatment of anthocyanins significantly (p < 0.05) enhanced the thymus and spleen indices and spleen cell survival compared to the irradiation control group. Pretreatment with anthocyanins before irradiation significantly reduced the numbers of micronuclei (MN) in bone marrow polychromatic erythrocytes (PCEs). These findings indicate that anthocyanins have immunostimulatory potential against immunosuppression induced by the radiation.
Peiffer, Daniel S; Zimmerman, Noah P; Wang, Li-Shu; Ransom, Benjamin W S; Carmella, Steven G; Kuo, Chieh-Ti; Siddiqui, Jibran; Chen, Jo-Hsin; Oshima, Kiyoko; Huang, Yi-Wen; Hecht, Stephen S; Stoner, Gary D
Diets containing either freeze-dried black raspberries (BRBs) or their polyphenolic anthocyanins (ACs) have been shown to inhibit the development of N-nitrosomethylbenzylamine (NMBA)-induced esophageal cancer in rats. The present study was conducted to determine whether PCA, a major microbial metabolite of black raspberry (BRB) ACs, also prevents NMBA-induced esophageal cancer in rats. F344 rats were injected with NMBA three times a week for 5 weeks and then fed control or experimental diets containing 6.1% BRBs, an anthocyanin (AC)-enriched fraction derived from BRBs, or protocatechuic acid (PCA). Animals were exsanguinated at weeks 15, 25, and 35 to quantify the development of preneoplastic lesions and tumors in the esophagus, and to relate this to the expression of inflammatory biomarkers. At weeks 15 and 25, all experimental diets were equally effective in reducing NMBA-induced esophageal tumorigenesis, as well as in reducing the expression of pentraxin-3 (PTX3), a cytokine produced by peripheral blood mononuclear cells in response to interleukin (IL)-1β and TNF-α. All experimental diets were also active at reducing tumorigenesis at week 35; however, the BRB diet was significantly more effective than the AC and PCA diets. Furthermore, all experimental diets inhibited inflammation in the esophagus via reducing biomarker (COX-2, iNOS, p-NF-κB, and sEH) and cytokine (PTX3) expression. Overall, our data suggest that BRBs, their component ACs, and PCA inhibit NMBA-induced esophageal tumorigenesis, at least in part, by their inhibitory effects on genes associated with inflammation. ©2014 American Association for Cancer Research.
Pineda-Vadillo, Carlos; Nau, Françoise; Guerin-Dubiard, Catherin; Jardin, Julien; Lechevalier, Valérie; Sanz-Buenhombre, Marisa; Guadarrama, Alberto; Tóth, Tamás; Csavajda, Éva; Hingyi, Hajnalka; Karakaya, Sibel; Sibakov, Juhani; Capozzi, Francesco; Bordoni, Alessandra; Dupont, Didier
The aim of the present study was to understand to what extent the inclusion of anthocyanins into dairy and egg matrices could affect their stability after processing and their release and solubility during digestion. For this purpose, individual and total anthocyanin content of four different enriched matrices, namely custard dessert, milkshake, pancake and omelettete, was determined after their manufacturing and during in vitro digestion. Results showed that anthocyanin recovery after processing largely varied among matrices, mainly due to the treatments applied and the interactions developed with other food components. In terms of digestion, the present study showed that the inclusion of anthocyanins into food matrices could be an effective way to protect them against intestinal degradation, and also the incorporation of anthocyanins into matrices with different compositions and structures could represent an interesting and effective method to control the delivery of anthocyanins within the different compartments of the digestive tract.
Bursać Kovačević, Danijela; Putnik, Predrag; Dragović-Uzelac, Verica; Vahčić, Nada; Babojelić, Martina Skendrović; Levaj, Branka
The objective of this study was to detect influences of cultivar, cultivation and processing on anthocyanin content and color in purees and low-sugar jams produced from strawberry cultivars (Elsanta, Maya, Marmolada, Queen Elisa), grown under conventional and organic cultivation. Color was determined by CIELab values while anthocyanins were quantified by HPLC-UV/VIS-PDA. Queen Elisa was the best cultivar for processing as it had highest total anthocyanin content (TAC) that was well preserved in processing. On average, processing purees to jams decreased TAC for 28% where pelargonidin-3-glucoside revealed most noticeable loss (53%) and cyanidin-3-rutinoside was best preserved in processing. Obtained results indicated that measurement of colorimetric parameters are strongly correlated with content of anthocyanins. In other words, loss of anthocyanins during processing was accompanied by noticeable decrease in lightness, red/yellow color and total color change. Results showed that change of color is useful predictor for estimating anthocyanins in strawberry purees and jams.
Zhang, Kai Ming; Wang, Jia Wan; Guo, Mei Li; Du, Wen Li; Wu, Rong Hua; Wang, Xian
The leaves of Begonia semperflorens accumulate anthocyanins and turn red in autumn in sub-temperate areas. This induction of anthocyanin biosynthesis in autumn has been attributed to the effects of low temperature, but the effects of different light regimes on this process are still being debated. In the present work, short days were found to be necessary for anthocyanin biosynthesis at low temperature. Under the same low-temperature conditions, Begonia seedlings grown under the short-day condition accumulated more carbohydrates and abscisic acid (ABA), which both induce anthocyanin biosynthesis. However, fewer carbohydrates and more gibberellin (GA) accumulated under the long-day conditions to maintain growth, which blocked anthocyanin biosynthesis and resulted in a lack of increases in the activities of dihydroflavonol 4-reductase (DFR) and flavonoid-3-O-glucosyl transferase (UFGT). Consequently, carbon flux, which was altered due to the blockade of anthocyanin synthesis, was channelled into the production of quercetin and phenolic acids but not lignin.
Natural variation for anthocyanin accumulation under high-light and low-temperature stress is attributable to the ENHANCER OF AG-4 2 (HUA2) locus in combination with PRODUCTION OF ANTHOCYANIN PIGMENT1 (PAP1) and PAP2.
Ilk, Nadine; Ding, Jia; Ihnatowicz, Anna; Koornneef, Maarten; Reymond, Matthieu
Growing conditions combining high light intensities and low temperatures lead to anthocyanin accumulation in plants. This response was contrasted between two Arabidopsis thaliana accessions, which were used to decipher the genetic and molecular bases underlying the variation of this response. Quantitative trait loci (QTLs) for flowering time (FT) and anthocyanin accumulation under a high-light and low-temperature scenario versus a control environment were mapped. Major QTLs were confirmed using near-isogenic lines. Candidate genes were examined using mutants and gene expression studies as well as transgenic complementation. Several QTLs were found for FT and for anthocyanin content, of which one QTL co-located at the ENHANCER OF AG-4 2 (HUA2) locus. That HUA2 is a regulator of both pathways was confirmed by the analysis of loss-of-function mutants. For a strong expression of anthocyanin, additional allelic variation was detected for the PRODUCTION OF ANTHOCYANIN PIGMENT1 (PAP1) and PAP2 genes which control the anthocyanin pathway. The genetic control of variation for anthocyanin content was dissected in A. thaliana and shown to be affected by a common regulator of flowering and anthocyanin biosynthesis together with anthocyanin-specific regulators. © 2014 INRA New Phytologist © 2014 New Phytologist Trust.
Srivastava, Anita; Akoh, Casimir C; Fischer, Joan; Krewer, Gerard
In recent years, considerable attention has been paid to anthocyanins due to their abilities to inhibit oxidative stress and cell proliferation. The regulations of apoptosis and the phase II enzymes glutathione-S-transferase (GST) and quinone reductase (QR) are other potential mechanisms through which flavonoids such as anthocyanins may prevent cancer. Our study confirmed that anthocyanin fractions from high bush blueberry cultivars increased apoptosis using two different methods: DNA fragmentation and caspase-3 activity. The effect of anthocyanins on the activity of the detoxifying enzymes GST and QR was also determined. Major anthocyanins identified were delphinidin, cyanidin, peonidin, petunidin, and malvidin. In Tifblue and Powderblue cultivars, DNA fragmentation increased at anthocyanin concentrations from 50 to 150 microg/mL, but cells treated with the anthocyanin fraction of Brightblue and Brightwell showed a prominent ladder at 50-100 microg/mL when compared to cells treated with 150 microg/mL. There was a significant difference in the caspase-3 activity (P < 0.05) between the control cells and the cells treated with anthocyanins from all of the cultivars. The response correlated positively with dose. The QR activity was lower in all cells treated with an anthocyanin fraction from Tifblue, Powderblue, Brightblue, and Brightwell cultivars than in control cells (P < 0.05). The activity decreased gradually when treated with increased concentrations of anthocyanin fractions (50-150 microg/mL) in the Tifblue and Powderblue cultivars. The GST activity was lower (P < 0.05) in cells treated with anthocyanin fractions from all of the cultivars and at all concentrations. These results indicated that apoptosis was confirmed in HT-29 cells when treated with anthocyanins from blueberry cultivars at 50-150 microg/mL concentrations, but these same concentrations decrease QR and GST activities rather than induce them.
Cremonini, Eleonora; Mastaloudis, Angela; Hester, Shelly N; Verstraeten, Sandra V; Anderson, Maureen; Wood, Steven M; Waterhouse, Andrew L; Fraga, Cesar G; Oteiza, Patricia I
An increased permeability of the intestinal barrier is proposed as a major event in the pathophysiology of conditions characterized by chronic gut inflammation. This study investigated the capacity of pure anthocyanins (AC), and berry and rice extracts containing different types and amounts of AC, to inhibit tumor necrosis alpha (TNFα)-induced permeabilization of Caco-2 cell monolayers. Caco-2 cells differentiated into intestinal epithelial cell monolayers were incubated in the absence/presence of TNFα, with or without the addition of AC or AC-rich plant extracts (ACRE). AC and ACRE inhibited TNFα-induced loss of monolayer permeability as assessed by changes in transepithelial electrical resistance (TEER) and paracellular transport of FITC-dextran. In the range of concentrations tested (0.25-1 μM), O-glucosides of cyanidin, and delphinidin, but not those of malvidin, peonidin and petunidin protected the monolayer from TNFα-induced decrease of TEER and increase of FITC-dextran permeability. Cyanidin and delphinidin acted by mitigating TNFα-triggered activation of transcription factor NF-κB, and downstream phosphorylation of myosin light chain (MLC). The protective actions of the ACRE on TNFα-induced TEER increase was positively correlated with the sum of cyanidins and delphinidins (r(2) = 0.83) content in the ACRE. However, no correlation was observed between TEER and ACRE total AC, malvidin, or peonidin content. Results support a particular capacity of cyanidins and delphinidins in the protection of the intestinal barrier against inflammation-induced permeabilization, in part through the inhibition of the NF-κB pathway.
Cress, Brady F; Leitz, Quentin D; Kim, Daniel C; Amore, Teresita D; Suzuki, Jon Y; Linhardt, Robert J; Koffas, Mattheos A G
Anthocyanins are a class of brightly colored, glycosylated flavonoid pigments that imbue their flower and fruit host tissues with hues of predominantly red, orange, purple, and blue. Although all anthocyanins exhibit pH-responsive photochemical changes, distinct structural decorations on the core anthocyanin skeleton also cause dramatic color shifts, in addition to improved stabilities and unique pharmacological properties. In this work, we report for the first time the extension of the reconstituted plant anthocyanin pathway from (+)-catechin to O-methylated anthocyanins in a microbial production system, an effort which requires simultaneous co-option of the endogenous metabolites UDP-glucose and S-adenosyl-L-methionine (SAM or AdoMet). Anthocyanin O-methyltransferase (AOMT) orthologs from various plant sources were co-expressed in Escherichia coli with Petunia hybrida anthocyanidin synthase (PhANS) and Arabidopsis thaliana anthocyanidin 3-O-glucosyltransferase (At3GT). Vitis vinifera AOMT (VvAOMT1) and fragrant cyclamen 'Kaori-no-mai' AOMT (CkmOMT2) were found to be the most effective AOMTs for production of the 3'-O-methylated product peonidin 3-O-glucoside (P3G), attaining the highest titers at 2.4 and 2.7 mg/L, respectively. Following modulation of plasmid copy number and optimization of VvAOMT1 and CkmOMT2 expression conditions, production was further improved to 23 mg/L using VvAOMT1. Finally, CRISPRi was utilized to silence the transcriptional repressor MetJ in order to deregulate the methionine biosynthetic pathway and improve SAM availability for O-methylation of cyanidin 3-O-glucoside (C3G), the biosynthetic precursor to P3G. MetJ repression led to a final titer of 51 mg/L (56 mg/L upon scale-up to shake flask), representing a twofold improvement over the non-targeting CRISPRi control strain and 21-fold improvement overall. An E. coli strain was engineered for production of the specialty anthocyanin P3G using the abundant and comparatively
Tarmizi, Ermiziar E-mail: firstname.lastname@example.org; Saragih, Raskita; Lalasari, Latifa Hanum E-mail: email@example.com
Anthocyanin from the red-color-melinjo peels could be isolated using a polar solvent (ethanol) [ermiziar, 2010]. The amount of hydrocarbons in the structure of anthocyanin might cause that anthocyanin could be isolated using a non polar solvent. The purpose of research is to isolate anthocyanin using non polar solvents (hexane and petroleum ether) with maceration steps for 24 hours and separate solvents using rotary evaporator equipment. The stability of anthocyanin could be observed every week (1,2,3 and 4 weeks) in various environmental conditions (with or without light in refrigerator and open or closed storage). The characterization of anthocyanin was analyzed with visual (physic photo) and or using equipments such as Fourier Transform Infrared Spectroscopy (FTIR) for determining functional groups, Ultraviolet–Visible Spectroscopy (UV/Vis) with 500-550 nm wavelengths for deciding absorption of anthocyanin and atomic absorption spectroscopy (AAS) for analyzing Fe element. The result showed that anthocyanin isolation with hexane solvent has yield higher than petroleum eter solvent. From the results of physic observation for 4 weeks looked that there are changing colors of samples significant after 3 and 4 weeks in cooler with or without light. The stability of anthocyanin color was the best on the storage time until 2 weeks using hexane solvent in refrigerator and closed condition that it has absorption of 0.6740 with 500 nm wavelengths and Fe concentration 6.29 ppm.
Tarmizi, Ermiziar; Lalasari, Latifa Hanum; Saragih, Raskita
Anthocyanin from the red-color-melinjo peels could be isolated using a polar solvent (ethanol) [ermiziar, 2010]. The amount of hydrocarbons in the structure of anthocyanin might cause that anthocyanin could be isolated using a non polar solvent. The purpose of research is to isolate anthocyanin using non polar solvents (hexane and petroleum ether) with maceration steps for 24 hours and separate solvents using rotary evaporator equipment. The stability of anthocyanin could be observed every week (1,2,3 and 4 weeks) in various environmental conditions (with or without light in refrigerator and open or closed storage). The characterization of anthocyanin was analyzed with visual (physic photo) and or using equipments such as Fourier Transform Infrared Spectroscopy (FTIR) for determining functional groups, Ultraviolet-Visible Spectroscopy (UV/Vis) with 500-550 nm wavelengths for deciding absorption of anthocyanin and atomic absorption spectroscopy (AAS) for analyzing Fe element. The result showed that anthocyanin isolation with hexane solvent has yield higher than petroleum eter solvent. From the results of physic observation for 4 weeks looked that there are changing colors of samples significant after 3 and 4 weeks in cooler with or without light. The stability of anthocyanin color was the best on the storage time until 2 weeks using hexane solvent in refrigerator and closed condition that it has absorption of 0.6740 with 500 nm wavelengths and Fe concentration 6.29 ppm.
Wang, Erlei; Liu, Yanjun; Xu, Caina; Liu, Jingbo
ABSTRACT Background: Anthocyanins have been proven to affect multiple cancer-associated processes in different cancer cell lines. However, relatively few studies have investigated the effects of blueberry anthocyanins on metastatic melanoma. Thus, this study focuses on evaluating the chemopreventive potential of blueberry anthocyanins and their aglycones (anthocyanidins) in B16-F10 melanoma cells. Methods: Blueberry anthocyanin and anthocyanidin extracts were prepared mainly by combined chromatography techniques. Their antiproliferative and proapoptotic effects on B16-F10 cells were evaluated by MTT assay, calcein acetoxymethyl ester/propidium iodide (calcein-AM/PI) staining, and flow cytometry of the cell cycle and apoptosis. Results: The MTT and calcein-AM/PI staining results showed that both anthocyanin (purity of 62.5%) and anthocyanidin (75.1%) extracts could significantly inhibit the viability and proliferation of B16-F10 cells in a dose-dependent manner, while anthocyanidin extracts exhibited significantly higher (p < 0.05) cytotoxicity than anthocyanin extracts. Furthermore, anthocyanin and anthocyanidin extracts blocked cell cycle procession at the G0/G1 phase below 400 and 200 μg/mL, and induced early apoptosis below 400 and 300 μg/mL, respectively. Conclusions: These data suggest that both anthocyanin and anthocyanidin extracts inhibit the proliferation and trigger the apoptosis of B16-F10 cells, and anthocyanidin extracts may be a more promising candidate in preventing metastatic melanoma than anthocyanin extracts. PMID:28680383
Zhang, Na; Qi, Yan; Zhang, Hai-Jun; Wang, Xiaoyun; Li, Hongfei; Shi, Yantong; Guo, Yang-Dong
Genistein (GNT), an isoflavone, is used in the clinical treatment of various health disorders. GNT is found in primary food source plants and some medical plants. However, studies on the functions of GNT in plants are rarely reported. In this study, we demonstrated that GNT plays an important role in promoting anthocyanin accumulation in red cabbage. GNT solutions (10, 20, 30, 40, and 50 mg/L) as foliar fertilizers were applied to red cabbage. Consequently, anthocyanin accumulation in red cabbage increased in a light-dependent manner. GNT solution at 30 mg/L exhibited the optimal effect on anthocyanin accumulation, which was twice that of the control. Quantitative real-time PCR analysis indicated that GNT application upregulated the expression of all structural genes, contributing to anthocyanin biosynthesis under light conditions. Under dark conditions, GNT exerted no significant promotive effect on anthocyanin accumulation; only early biosynthetic genes of anthocyanin biosynthesis responded to GNT. The promotive effect of GNT on anthocyanin biosynthesis is directly attributable to the regulation of structural gene expression. Transcription factors exhibited no response to GNT. The levels of anthocyanin in red cabbage positively correlated with the enzyme activities of antioxidant systems. This finding correlation suggested that the promotive effect of GNT on anthocyanin levels was correlated with improved antioxidant activity in the red cabbage. PMID:27990149
Szalóki-Dorkó, Lilla; Ladányi, Márta; Ficzek, Gitta; Stéger-Máté, Mónika
Summary Sour cherry juices made from two sour cherry cultivars (Érdi bőtermő and Kántorjánosi 3) were investigated to determine their total anthocyanin content and half-life of anthocyanins during heat treatment at different temperatures (70, 80 and 90 °C) for 4 h. Before the heat treatment, Érdi bőtermő juice had higher anthocyanin concentration (812 mg/L) than Kántorjánosi 3 juice (513 mg/L). The greatest heat sensitivity of anthocyanins was measured at 90 °C, while the treatments at 80 and 70 °C caused lower thermal degradation. The loss of anthocyanins in Érdi bőtermő juice after treatment was 38, 29 and 18%, respectively, while in Kántorjánosi 3 juice losses of 46, 29 and 19% were observed, respectively. At 90 °C sour cherry Érdi bőtermő juice had higher half-life (t1/2) of anthocyanins, while the Kántorjánosi 3 juice had higher t1/2 values at 70 °C. Cyanidin-3-glucosyl-rutinoside was present in higher concentrations in both cultivars (Érdi bőtermő: 348 and Kántorjánosi 3: 200 mg/L) than cyanidin-3-rutinoside (177 and 121 mg/L) before treatment. However, during the experiment, cyanidin-3-rutinoside was proved to be more resistant to heat. Comparing the two varieties, both investigated pigment compounds were more stable in Kántorjánosi 3 than in Érdi bőtermő. Degradation rate of anthocyanins was cultivar-dependent characteristic, which should be taken into account in the food production. PMID:27904369
Alfenito, M R; Souer, E; Goodman, C D; Buell, R; Mol, J; Koes, R; Walbot, V
Glutathione S-transferases (GSTs) traditionally have been studied in plants and other organisms for their ability to detoxify chemically diverse herbicides and other toxic organic compounds. Anthocyanins are among the few endogenous substrates of plant GSTs that have been identified. The Bronze2 (Bz2) gene encodes a type III GST and performs the last genetically defined step of the maize anthocyanin pigment pathway. This step is the conjugation of glutathione to cyanidin 3-glucoside (C3G). Glutathionated C3G is transported to the vacuole via a tonoplast Mg-ATP-requiring glutathione pump (GS-X pump). Genetically, the comparable step in the petunia anthocyanin pathway is controlled by the Anthocyanin9 (An9) gene. An9 was cloned by transposon tagging and found to encode a type I plant GST. Bz2 and An9 have evolved independently from distinct types of GSTs, but each is regulated by the conserved transcriptional activators of the anthocyanin pathway. Here, a phylogenetic analysis is presented, with special consideration given to the origin of these genes and their relaxed substrate requirements. In particle bombardment tests, An9 and Bz2 functionally complement both mutants. Among several other GSTs tested, only soybean GmGST26A (previously called GmHsp26A and GH2/4) and maize GSTIII were found to confer vacuolar sequestration of anthocyanin. Previously, these genes had not been associated with the anthocyanin pathway. Requirements for An9 and Bz2 gene function were investigated by sequencing functional and nonfunctional germinal revertants of an9-T3529, bz2::Ds, and bz2::Mu1. PMID:9668133
Buchweitz, M; Speth, M; Kammerer, D R; Carle, R
The objective of the present study was to evaluate the effects of different pectins on strawberry anthocyanins in viscous model solutions at pH 3.0. For this purpose, low esterified amidated, low and high methyl esterified citrus and apple pectins, and a sugar beet pectin (SBP), respectively, were added to strawberry extracts. The latter were predominantly composed of pelargonidin-glycosides, containing either reduced (E-1) or original amounts of non-anthocyanin phenolics (E-2). Model systems were stored for 18 weeks at 20±0.5 °C protected from light, and anthocyanins were quantitated in regular intervals by HPLC-DAD analyses. Half-life (t1/2) and destruction (D) values were calculated based on first-order kinetics. Generally, significant differences in pigment retention could be ascribed to differing pectin sources, while variation in the degree of esterification and amidation, respectively, had negligible effects. Compared to systems without added pectin, apple pectins and SPB enhanced anthocyanin stability moderately, while stabilising effects of citrus pectins were poor or even imperceptible. Generally, the amount of non-anthocyanin phenolics and the addition of citrate did not markedly affect anthocyanin stability. However, pectins had no influence on total phenolic contents (Folin-Ciocalteu assay) and antioxidant capacities (FRAP and TEAC assay) of strawberry phenolics over time. For pelargonidin-3-glucoside and -rutinoside largely consistent stabilities were found in all model systems. In contrast, pelargonidin-3-malonylglucoside was less stable in the blank, and stabilisation by pectins was always negligible. The findings of the present study are contrary to results reported previously for the stabilisation of cyanidin- and delphinidin-glycosides in similar model systems prepared with black currant extracts, indicating a high impact of the number of hydroxyl groups in the anthocyanin B-ring. Copyright © 2013 Elsevier Ltd. All rights reserved.
Background Plant color variation is due not only to the global pigment concentration but also to the proportion of different types of pigment. Variation in the color spectrum may arise from secondary modifications, such as hydroxylation and methylation, affecting the chromatic properties of pigments. In grapes (Vitis vinifera L.), the level of methylation modifies the stability and reactivity of anthocyanin, which directly influence the color of the berry. Anthocyanin methylation, as a complex trait, is controlled by multiple molecular factors likely to involve multiple regulatory steps. Results In a Syrah × Grenache progeny, two QTLs were detected for variation in level of anthocyanin methylation. The first one, explaining up to 27% of variance, colocalized with a cluster of Myb-type transcription factor genes. The second one, explaining up to 20% of variance, colocalized with a cluster of O-methyltransferase coding genes (AOMT). In a collection of 32 unrelated cultivars, MybA and AOMT expression profiles correlated with the level of methylated anthocyanin. In addition, the newly characterized AOMT2 gene presented two SNPs associated with methylation level. These mutations, probably leading to a structural change of the AOMT2 protein significantly affected the enzyme specific catalytic efficiency for the 3'-O-methylation of delphinidin 3-glucoside. Conclusion We demonstrated that variation in methylated anthocyanin accumulation is susceptible to involve both transcriptional regulation and structural variation. We report here the identification of novel AOMT variants likely to cause methylated anthocyanin variation. The integration of QTL mapping and molecular approaches enabled a better understanding of how variation in gene expression and catalytic efficiency of the resulting enzyme may influence the grape anthocyanin profile. PMID:22171701
Hughes, Nicole M; Carpenter, Kaylyn L; Cannon, Jonathan G
The association between plant water stress and synthesis of red, anthocyanin pigments in leaves has led some plant biologists to propose an osmotic function of leaf reddening. According to this hypothesis, anthocyanins function as a solute in osmotic adjustment (OA), contributing to depression of osmotic potential (Ψ(π)) and maintenance of turgor pressure during drought-stressed conditions. Here we calculate the percent contribution of anthocyanin to leaf Ψ(π) during OA in two angiosperm evergreen species, Galax urceolata and Gaultheria procumbens. Both species exhibit dramatic leaf reddening under high light during winter, concomitant with declines in leaf water potential and accumulation of solutes. Data previously published by the authors on osmotic potential at full turgor (Ψ(π,100)) of G. urceolata and G. procumbens leaves before and after leaf reddening were used to estimate OA. In vivo molar concentrations of anthocyanin, glucose, fructose, and sucrose measured from the same individuals were converted to pressure equivalents using the Ideal Gas Law, and percent contribution to OA was estimated. Estimated mean OA during winter was -0.7MPa for G. urceolata and -0.8MPa for G. procumbens. In vivo concentrations of anthocyanin (3-10mM) were estimated to account for ∼2% of OA during winter, and comprised <0.7% of Ψ(π,100) in both species. Glucose, fructose, and sucrose combined accounted for roughly 50 and 80% of OA for G. urceolata and G. procumbens, respectively, and comprised ∼20% of Ψ(π,100). We observed that a co-occurring, acyanic species (Vinca minor) achieved similar OA without synthesizing anthocyanin. We conclude that anthocyanins represent a measurable, albeit meager, component of OA in red-leafed evergreen species during winter. However, due to their low concentrations, metabolic costliness relative to other osmolytes, and striking red color (unnecessary for an osmotic function), it is unlikely that they are synthesized solely for an
Qu, Jun-Ge; Yu, Xing-Ju; Zhang, Wei; Jin, Mei-Fang
The low-production is a ubiquitous problem and has prevented the commercialization of secondary metabolite production in plant cell culture. In order to examine the effective approaches to improvement of secondary metabolite production in plant cell culture, the investigation of anthocyanins accumulation in suspension cultures of Vitis vinifera, as a model system, had been initiated in our laboratory. In this present research, various elicitors and the precursor of phenylalanine were used in combination to enhance the anthocyanins production in suspension cultures of Vitis vinifera. And an integrated process with the combination of elicitation, precursor feeding and light irradiation was reported for rational bioprocess design. Among the combination treatment of phenylalanine feeding and several elicitors (methyl-beta-cyclodextrin, dextran T-40, methyl jasmonate, extracts of Aspergillus niger and Fusarium orthoceras), the combination with methyl jasmonate gave the highest anthocyanins production in suspension cultures of Vitis vinifera. When compared to the controls, the anthocyanins content (CV/g, FCW) and production (CV/L) increased by 2.7-fold and 3.4-fold, respectively. The optimum time for the addition of phenylalanine and methyl jasmonate was 4 days after inoculation. Two cell lines with different anthocyanins-producing capacity responded differently to the optimum combination treatment of 30 micromol/L phenylalanine feeding, 218 micromol/L methyl jasmonate elicitation and 3000 to approximately 4000 1x light illumination. The high-and low-anthocyanins-producing cell lines of VV05 and VV06 produced the maximum of 2975 and 4090 CV/L of anthocyanins that were 2.5- and 5.2-fold of the controls, respectively.
Cheng, Guo; He, Yan-Nan; Yue, Tai-Xin; Wang, Jun; Zhang, Zhen-Wen
Climatic conditions and soil type have significant influence on grape ripening and wine quality. The reported study was conducted in two "Cabernet Sauvignon (Vitis vinifera L.V)" vineyards located in Xinjiang, a semiarid wine-producing region of China during two vintages (2011 and 2012). The results indicate that soil and climate affected berry growth and anthocyanin profiles. These two localities were within a distance of 5 km from each other and had soils of different physical and chemical composition. For each vineyard, the differences of anthocyanin concentrations, and parameters concerning berry growth and composition between the two years could be explained by different climatic conditions. Soil effect was studied by investigation of differences in berry composition and anthocyanin profiles between the two vineyards in the same year, which could be explained mainly by the different soil properties, vine water and nitrogen status. Specifically, the soils with less water and organic matter produced looser clusters, heavier berry skins and higher TSS, which contributed to the excellent performance of grapes. Compared with 2011, the increases in anthocyanin concentrations for each vineyard in 2012 could be attributed to smaller number of extreme temperature (>35 °C) days and rainfall, lower vine water status and N level. The explanation for higher anthocyanin concentrations in grape skins from the soils with less water and organic matter could be the vine status differences, lighter berry weight and heavier skin weight at harvest. In particular, grapes from the soils with less water and organic matter had higher levels of 3'5'-substituded, O-methylated and acylated anthocyanins, which represented a positive characteristic conferring more stable pigmentation to the corresponding wine in the future. The present work clarifies the effects of climate and soil on berry growth and anthocyanin profiles, thus providing guidance for production of high-quality wine grapes
Alongi, Kristin S; Padilla-Zakour, Olga I; Sacks, Gavin L
The color of Concord grape juice produced by concentration before cold-stabilization and detartration (direct-to-concentrate, DTC) was compared to juice produced via cold-stabilization prior to concentration (standard concentrate, SC) and evaluated by several metrics. Using the Boulton copigmentation assay, the majority of the absorbance at 520 nm in bottled SC juice (72%) was due to monomeric anthocyanins. Following reconstitution, DTC juice had a 63% greater absorbance at 520 nm than SC juice. A significant loss of anthocyanins was observed using a paired t test during cold-stabilization of single-strength juice during SC processing (mean loss: 79 mg/L as cyanidin-3-glucoside, 23% of total anthocyanins), while no significant loss of anthocyanins or change in other color metrics was observed during cold-stabilization of DTC concentrate. The concentration of anthocyanins in the SC bitartrate crystals was 0.80% w/w compared to 0.13% w/w in the DTC bitartrate crystals. Between DTC and SC, no difference in copigmentation was observed in cold-stabilized concentrate or reconstituted juice, indicating that the increased stability of anthocyanins could not be credited to greater copigmentation in DTC during detartration. HPLC analyses indicated that anthocyanin species with higher pKh and thus proportionally greater flavylium ion concentration at juice pH are preferentially lost during SC processing. The proportional changes in color metrics during shelf life stability testing (0-16 weeks, 2-30 °C) were not significantly different between SC and DTC juices.
Ludwig, Iziar A; Mena, Pedro; Calani, Luca; Borges, Gina; Pereira-Caro, Gema; Bresciani, Letizia; Del Rio, Daniele; Lean, Michael E J; Crozier, Alan
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 1-1.5h 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.
Jin, Wanmei; Wang, Hua; Li, Maofu; Wang, Jing; Yang, Yuan; Zhang, Xiaoming; Yan, Guohua; Zhang, Hong; Liu, Jiashen; Zhang, Kaichun
Sweet cherry is a diploid tree species and its fruit skin has rich colours from yellow to blush to dark red. The colour is closely related to anthocyanin biosynthesis and is mainly regulated at the transcriptional level by transcription factors that regulate the expression of multiple structural genes. However, the genetic and molecular bases of how these genes ultimately determine the fruit skin colour traits remain poorly understood. Here, our genetic and molecular evidences identified the R2R3 MYB transcription factor PavMYB10.1 that is involved in anthocyanin biosynthesis pathway and determines fruit skin colour in sweet cherry. Interestingly, we identified three functional alleles of the gene causally leading to the different colours at mature stage. Meanwhile, our experimental results of yeast two-hybrid assays and chromatin immunoprecipitation assays revealed that PavMYB10.1 might interact with proteins PavbHLH and PavWD40, and bind to the promoter regions of the anthocyanin biosynthesis genes PavANS and PavUFGT; these findings provided to a certain extent mechanistic insight into the gene's functions. Additionally, genetic and molecular evidences confirmed that PavMYB10.1 is a reliable DNA molecular marker to select fruit skin colour in sweet cherry. © 2016 The Authors. Plant Biotechnology Journal published by Society for Experimental Biology and The Association of Applied Biologists and John Wiley & Sons Ltd.