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Sample records for acylated anthocyanin transporters1woa

  1. Stability-increasing effects of anthocyanin glycosyl acylation.

    Zhao, Chang-Ling; Yu, Yu-Qi; Chen, Zhong-Jian; Wen, Guo-Song; Wei, Fu-Gang; Zheng, Quan; Wang, Chong-De; Xiao, Xing-Lei

    2017-01-01

    This review comprehensively summarizes the existing knowledge regarding the chemical implications of anthocyanin glycosyl acylation, the effects of acylation on the stability of acylated anthocyanins and the corresponding mechanisms. Anthocyanin glycosyl acylation commonly refers to the phenomenon in which the hydroxyl groups of anthocyanin glycosyls are esterified by aliphatic or aromatic acids, which is synthetically represented by the acylation sites as well as the types and numbers of acyl groups. Generally, glycosyl acylation increases the in vitro and in vivo chemical stability of acylated anthocyanins, and the mechanisms primarily involve physicochemical, stereochemical, photochemical, biochemical or environmental aspects under specific conditions. Additionally, the acylation sites as well as the types and numbers of acyl groups influence the stability of acylated anthocyanins to different degrees. This review could provide insight into the optimization of the stability of anthocyanins as well as the application of suitable anthocyanins in food, pharmaceutical and cosmetic industries. PMID:27507456

  2. Enzymatic Acylation of Anthocyanin Isolated from Black Rice with Methyl Aromatic Acid Ester as Donor: Stability of the Acylated Derivatives.

    Yan, Zheng; Li, Chunyang; Zhang, Lixia; Liu, Qin; Ou, Shiyi; Zeng, Xiaoxiong

    2016-02-10

    The enzymatic acylation of anthocyanin from black rice with aromatic acid methyl esters as acyl donors and Candida antarctica lipase B was carried out under reduced pressure. The highest conversion of 91% was obtained with benzoic acid methyl ester as acyl donor; cyanidin 3-(6″-benzoyl)-glucoside, cyanidin 3-(6″-salicyloyl)-glucoside, and cyanidin 3-(6″-cinnamoyl)-glucoside were successfully synthesized. This is the first report on the enzymatic acylation of anthocyanin from black rice with methyl aromatic esters as acyl donors and lipase as biocatalyst. Furthermore, the acylation with aromatic carboxylic acids enhanced both the thermostability and light resistivity of anthocyanin. In particular, cyanidin 3-(6″-cinnamoyl)-glucoside was the most stable among the three acylated anthocyanins synthesized. PMID:26766135

  3. A New Acylated Anthocyanin from the Red Flowers of Camellia hongkongensis and Characterization of Anthocyanins in the Section Camellia Species

    Jian-Bin Li; Fumio Hashimoto; Keiichi Shimizu; Yusuke Sakata

    2009-01-01

    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)-β-galactopyranoside (6), two known acylated anthocyanins, cyanidin 3-O-(6-O-(E)-p-coumaroyl)-β-galactopyranoside (7) and cyanidin 3-O-(6-O-(E)-caffeoyl)-β-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.

  4. Acylated anthocyanins from sprouts of Raphanus sativus cv. Sango: isolation, structure elucidation and antioxidant activity.

    Matera, Riccardo; Gabbanini, Simone; Berretti, Serena; Amorati, Riccardo; De Nicola, Gina Rosalinda; Iori, Renato; Valgimigli, Luca

    2015-01-01

    Little is known on structure-activity relationships of antioxidant anthocyanins. Raphanus sativus cv Sango sprouts are among the richest sources (270 mg/100 g fresh weight). We isolated from sprouts' juice 9 acylated anthocyanins, including 4 new compounds. All comprise a cyanidin core bearing 3-4 glucose units, multiply acylated with malonic and phenolic acids (ferulic and sinapic). All compounds were equally effective in inhibiting the autoxidation of linoleic acid in aqueous micelles, with rate constant for trapping peroxyl radicals kinh=(3.8 ± 0.7) × 10(4)M(-1)s(-1) at 37 °C. In acetonitrile solution kinh varied with acylation: (0.9-2.1) × 10(5)M(-1)s(-1) at 30 °C. Each molecule trapped a number n of peroxyl radicals ranging from 4 to 7. Anthocyanins bearing sinapic acid were more effective than those bearing the ferulic moiety. Under identical settings, deacylated cyanin, ferulic and sinapic acids had kinh of 0.4 × 10(5), 0.3 × 10(5) and 1.6 × 10(5)M(-1)s(-1) respectively, with n ranging 2-3. Results show the major role of acylation on antioxidant performance. PMID:25053073

  5. High concentrations of aromatic acylated anthocyanins found in cauline hairs in Plectranthus ciliatus.

    Jordheim, Monica; Calcott, Kate; Gould, Kevin S; Davies, Kevin M; Schwinn, Kathy E; Andersen, Øyvind M

    2016-08-01

    Vegetative shoots of a naturalized population of purple-leaved plectranthus (Plectranthus ciliatus, Lamiaceae) were found to contain four main anthocyanins: peonidin 3-(6″-caffeoyl-β-glucopyranoside)-5-β-glucopyranoside, peonidin 3-(6″-caffeoyl-β-glucopyranoside)-5-(6‴-malonyl-β-glucopyranoside), peonidin 3-(6″-E-p-coumaroyl-β-glucopyranoside)-5-(6‴-malonyl-β-glucopyranoside), and peonidin 3-(6″-E-p-coumaroyl-β-glucopyranoside)-5-β-glucopyranoside. The first three of these pigments have not been reported previously from any plant. They all follow the typical anthocyanin pattern of Lamiaceae, with universal occurrence of anthocyanidin 3,5-diglucosides and aromatic acylation with p-coumaric and sometimes caffeic acids; however, they differ by being based on peonidin. The four anthocyanins were present in the leaves (22.2 mg g(-1) DW), and in the xylem and interfascicular parenchyma of the stem. They were exceptionally abundant, among the highest reported for any plant organ, in epidermal hairs on some of the stem internodes (101 mg g(-1) DW). Anthocyanin content in these hairs increased more than three-fold from the youngest to the fourth-youngest internodes. In situ absorbances (λmax ≈ 545 nm) were bathochromic in comparison to absorbances of the isolated anthocyanins in their flavylium form in acidified aqueous solutions (λmax = 525 nm), suggesting that the anthocyanins occur both in quinoidal and flavylium forms in constant proportions in the anthocyanic hair cells. The most distinctive observation with respect to relative proportions of individual anthocyanins was found in de-haired internodes, for which anthocyanin caffeoyl-derivatives decreased, and anthocyanin coumaroyl-derivatives increased, from the youngest to the fourth-youngest internode. PMID:27165277

  6. New acylated anthocyanins and other flavonoids from the red flowers of Clematis cultivars.

    Hashimoto, Masanori; Suzuki, Toshisada; Iwashina, Tsukasa

    2011-11-01

    Six new acylated cyanidin glycosides, cyanidin 3-O-beta-(2''-E-caffeoylglucopyranosyl)-(1 --> 2)-O-beta-galactopyranoside (1), cyanidin 3-O-beta-(2''-E-caffeoylglucopyranosyl)-(1 --> 2)-O-beta-(6''-malonylgalactopyranoside) (2), cyanidin 3-O-beta-(2''-E-caffeoylglucopyranosyl)-(1 --> 2)-O-beta-(6''-succinylgalactopyranoside) (3), cyanidin 3-O-beta-(2''-E-caffeoylglucopyranosyl)-(1 --> 2)-O-beta-galactopyranoside-3''- O-beta-glucuronopyranoside (4), cyanidin 3-O-beta-(2''-E-caffeoylglucopyranosyl)-(1 --> 2)-O-beta-(6''-malonylgalactopyranoside)-3'-O-beta-glucuronopyranoside (5), and cyanidin 3-O-beta-(2'-E-feruloylglucopyranosyl)-(1 --> 2)-O-beta-(6''-malonylgalactoside)-3' -O-beta-glucuronopyranoside (6), were isolated from the red flowers of two Clematis cultivars, 'Niobe'and 'Madame Julia Correvon'. The chemical structures of the isolated anthocyanins were determined by UV, LC-MS, HPLC, TLC, characterization of hydrolysates, and 1H and 13C NMR spectroscopy, including H-H COSY, C-H COSY, HMBC, HMQC and NOESY. The last three anthocyanins were widely distributed in 37 red flower Clematis cultivars. On the other hand, the first three compounds were found only in two cultivars. Five known flavonol glycosides, kaempferol 3-O-glucoside, kaempferol 3-O-rutinoside, quercetin 3-O-galactoside, quercetin 3-O-glucoside and quercetin 3-O-rutinoside, were isolated from the flowers of'Madame Julia Correvon'. PMID:22224277

  7. Bioavailability of Anthocyanins from Purple Carrot Juice: Effects of Acylation and Plant Matrix

    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, ...

  8. Study on stability and oxygen radicals scavenging capacity of acylated blueberries anthocyanins%酰基化蓝莓花色苷的稳定性和对氧自由基清除能力

    李颖畅; 李冰心; 吕春茂; 孟宪军

    2012-01-01

    The instability of natural anthocyanins was a big obstacle for its usage in food as colorants.In order to improve the stability of anthocyanins, molecular modification was used.The molecular modification of blueberry anthocyanins by acylation, the light, thermal stability and scavenging oxygen radicals of acylated anthocyanins were studied.The UV absorption spectrum and infrared spectrum showed that the blueberry anthocyanins had been acylated.Light and heat stability of acylated anthocyanins were significantly increased being compared with no acylated anthocyanins, but the capability of acylated anthocyanins on scavenging the hydroxyl radical, superoxide anion radical were weaker than those no acylated anthocyanins.lC~0 of scavenging hydroxyl radical and superoxide anion was 0.74,3.14mg/mL, respectively.%由于天然花色苷稳定性差,严重阻碍了其在食品工业中的广泛应用。为了改善花色苷的稳定性,采用分子修饰的方法,通过酰基化反应修饰蓝莓花色苷,并研究酰化后蓝莓花色苷的光、热稳定性和对氧自由基的清除能力。通过紫外吸收光谱和红外光谱表明蓝莓花色苷已经酰基化。相对未酰化的蓝莓花色苷,酰基化蓝莓花色苷的光、热稳定性显著提高,但清除羟基自由基、超氧阴离子自由基的能力略有下降,清除羟自由基、超氧阴离子自由基的IC,。分别为0.74、3.14mg/mL。

  9. Characterization of Acylated Anthocyanins in Callus Induced From Storage Root of Purple-Fleshed Sweet Potato, Ipomoea batatas L

    Terahara N.; Konczak I.; Ono H.; Yoshimoto M.; Yamakawa O.

    2004-01-01

    Four anthocyanins were isolated from a highly pigmented callus induced from the storage root of purple-fleshed sweet potato (Ipomoea batatas L) cultivar Ayamurasaki. The anthocyanins were respectively identified as cyanidin 3- O -(2- O -(6- O -( E )-caffeoyl- β -D-glucopyranosyl)- β -D-glucopyranoside)-5- O - β -D-glucopyranoside, cyanidin 3- O -(2- O -(6- O -( E )- p -coumaroyl- β -D-glucopyranosyl)-6- O -( E )-caffeoyl- β -D-glucopyranoside)-5- O -...

  10. Anthocyanin pigments in strawberry

    Lopes-da-Silva, M.F.; Escribano-Bailón, M.T.; Perez-Alonso, J.J.; Rivas-Gonzalo, J.C.; Santos-Buelga, Celestino

    2007-01-01

    The anthocyanin composition was analysed in strawberry fruits from five different cultivars (cv. Eris, Oso Grande, Carisma, Tudnew and Camarosa). Twenty-five defined anthocyanin pigments were detected, most of them containing Pelargonidin (Pg) as aglycone; some cyanidin (Cy) derivatives were also found. Glucose and rutinose were the usual substituting sugars, although arabinose and rhamnose were also tentatively identified; some minor anthocyanins showed acylation with aliphatic acids. A rele...

  11. LC-PDA-EIS/MSn identification of new anthocyanins in purple radish (Raphanus sativus L. variety)

    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...

  12. KARAKTERISTIK WARNA DAN AKTIVITAS ANTIOKSIDAN ANTOSIANIN UBI JALAR UNGU [Color Characteristics and Antioxidant Activity of Anthocyanin Extract from Purple Sweet Potato

    Ai Mahmudatussa’adah1,2)*; Dedi Fardiaz2); Nuri Andarwulan1,3); dan Feri Kusnandar1,3)

    2014-01-01

    Anthocyanin is a natural pigment that produces a range of colors, varying from red, purple, blue to yellow. The stability of the anthocyanin color is affected by pH, temperature, and light. Purple sweet potato is rich in anthocyanin, particularly a stable acylated anthocyanin. This research was conducted to study the effect of pH on color and antioxidative activity of anthocyanin extracted from purple sweet potatoes, harvested from Cilembu-Sumedang, Banjaran-Bandung, and Pakembangan-Kuningan....

  13. Achievements and perspectives in biochemistry concerning anthocyanin modification for blue flower coloration.

    Sasaki, Nobuhiro; Nakayama, Toru

    2015-01-01

    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. PMID:25015943

  14. Anthocyanins and heart disease

    Anthocyanins are red, blue, and purple pigments distributed throughout nature, and in our diet. One potential health benefit of dietary anthocyanins is protection against cardiovascular disease (CVD). Evidence for beneficial effects of anthocyanins with respect to heart disease comes from epidemio...

  15. Anthocyanin Accumulation, Antioxidant Ability and Stability, and a Transcriptional Analysis of Anthocyanin Biosynthesis in Purple Heading Chinese Cabbage (Brassica rapa L. ssp. pekinensis).

    He, Qiong; Zhang, Zhanfeng; Zhang, Lugang

    2016-01-13

    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. PMID:26709726

  16. Hydrophilic interaction chromatographic analysis of anthocyanins.

    Willemse, Chandré M; Stander, Maria A; de Villiers, André

    2013-12-01

    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. PMID:24188998

  17. Bioavailability of anthocyanins.

    Fang, Jim

    2014-11-01

    Anthocyanins are a subgroup of flavonoids responsible for the blue, purple, and red color of many fruits, flowers, and leaves. Consumption of foods rich in anthocyanins has been associated with a reduced risk of cardiovascular disease and cancer. The fate of anthocyanins after oral administration follows a unique pattern rather different from those of other flavonoids. Anthocyanins could be absorbed from the stomach as well as intestines. Active transporters may play a role in the absorption of anthocyanins from the stomach as well as in their transfer within the kidney or liver. Anthocyanins such as cyanidin-3-glucoside and pelargonidin-3-glucoside could be absorbed in their intact form into the gastrointestinal wall; undergo extensive first-pass metabolism; and enter the systemic circulation as metabolites. Phenolic acid metabolites were found in the blood stream in much higher concentrations than their parent compounds. These metabolites could be responsible for the health benefits associated with anthocyanins. Some anthocyanins can reach the large intestine in significant amounts and undergo decomposition catalyzed by microbiota. In turn, these decomposition products may contribute to the health effects associated with anthocyanins in the large intestine. This review comprehensively summarizes the existing knowledge about absorption, distribution, metabolism, and elimination of anthocyanins as well as their decomposition within the gastrointestinal lumen. PMID:25347327

  18. Temperature dependency of shelf and thermal stabilities of anthocyanins from corn distillers' dried grains with solubles in different ethanol extracts and a commercially available beverage.

    de Mejia, Elvira Gonzalez; Dia, Vermont P; West, Leslie; West, Megan; Singh, Vijay; Wang, Zhaoqin; Allen, Charlotte

    2015-11-18

    The objective was to determine the shelf and thermal stabilities of anthocyanins from distillers' dried grains with solubles (DDGS) extracted with different ethanol concentrations as well as a semi-purified Maiz Morado (purple corn) anthocyanin extract added to a commercially available beverage. Storage for 6 weeks of DDGS showed an overall reduction of anthocyanins from 6.8 to 73.7%. In DDGS, an ethanol increase from 0 to 25% resulted in less sensitivity of anthocyanin to temperature changes. Acylation resulted in faster degradation and higher reaction rate constants than their corresponding non-acylated forms. Anthocyanin changes were accompanied by an overall increase in lightness and a decrease in redness. Storage of beverage for 12 weeks at 4 °C resulted in a 25.5% reduction of anthocyanin. Results have important implications in selecting colored corn as an economical source of food colorants. PMID:26556543

  19. Relation Between Anthocyanin Structures and Color in Red Wine: a Review%红葡萄酒花色苷结构和颜色的关系研究进展

    韩富亮; 李杨; 李记明; 徐岩

    2011-01-01

    花色苷是红葡萄酒颜色的主要物质基础.本文根据花色苷结构,对其进行了分类,即基本花色苷(非酰化花色苷)、酰化花色苷、吡喃花色苷和聚合花色苷;并对其结构和颜色的关系进行了综述讨论,为葡萄酒颜色机理的研究提供参考.%Anthocyanins are responsible for red wine color. In this review , the anthocyanins are classified into four groups according to their structure: common anthocyanins (non-acylated anthocyanins), acylated anthocyanins, pyranoanthocyanins and polymeric anthocyanins; then expatiate on their contribution for wine color based on their structures in order to better understand the color changing mechanism of red wine.

  20. Chemical taxonomy of red-flowered wild Camellia species based on floral anthocyanins.

    Li, Jian-Bin; Hashimoto, Fumio; Shimizu, Keiichi; Sakata, Yusuke

    2013-01-01

    This study uses anthocyanins in the red flowers of section Camellia as taxonomic markers to investigate the phenetic relationships among 33 wild species from China, Taiwan, and Japan. The 25 anthocyanins from section Camellia produced 38 pigment patterns that serve as phenetic markers. Principal Component Analysis (PCA) indicated that the attachment of one or two glucoses to the cyanidin-core structure at the 3- or the 3- and 5-positions, respectively, was the most influential pattern against the first factor, Z₁. In addition, two alternative pigment patterns, acylated or non-acylated, and the structural isomerism (cis- or trans-) of the p-coumaroyl group were relatively significant patterns. Ward's minimum-variance cluster analysis (WMVCA) produced a dendrogram that consisted of two sub-clusters. One sub-cluster (A) was constructed by species that have mainly two types of anthocyanins: 3,5-di-O-β-glucosides (Camellia saluenensis) and sambubioside of cyanidin (Camellia reticulata). The other sub-cluster (B) was made up of the 3-O-β-glucosides of cyanidin (Camellia japonica) and delphinidin (Camellia hongkongensis), with a higher proportion of the 3-O-β-galactosides (Camellia mairei and Camellia boreali-yunnanica). The former group showed a higher proportion of acylation, over 63%, but with the exception of Camellia azalea. The latter group showed less than 52% acylation, but with the exception of C. hongkongensis and C. boreali-yunnanica. PCA and WMVCA indicated that the greater the amount of di-O-glycosides and acylation, the more primitive anthocyanin traits the species possess. Based on these results, in conjunction with geographical and literary information, the data suggest that the Xinan district is the site/center of origin for the red-flowered Camellia species of which both C. saluenensis and C. reticulata have the most primitive anthocyanin traits. PMID:23122772

  1. Anthocyanins Present in Some Tropical Fruits.

    Many tropical fruits are rich in anthocyanins, though limited information is available about the characterization and quantification of these anthocyanins. The identification of anthocyanin pigments in four tropical fruits was determined by ion trap mass spectrometry. Fruits studied included acero...

  2. Anthocyanin analyses of Vaccinium fruit dietary supplements

    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...

  3. Principal Component Regression Analysis of the Relation Between CIELAB Color and Monomeric Anthocyanins in Young Cabernet Sauvignon Wines

    Chang-Qing Duan

    2008-11-01

    Full Text Available Color is one of the key characteristics used to evaluate the sensory quality of red wine, and anthocyanins are the main contributors to color. Monomeric anthocyanins and CIELAB color values were investigated by HPLC-MS and spectrophotometry during fermentation of Cabernet Sauvignon red wine, and principal component regression (PCR, a statistical tool, was used to establish a linkage between the detected anthocyanins and wine coloring. The results showed that 14 monomeric anthocyanins could be identified in wine samples, and all of these anthocyanins were negatively correlated with the L*, b* and H*ab values, but positively correlated with a* and C*ab values. On an equal concentration basis for each detected anthocyanin, cyanidin-3-O-glucoside (Cy3-glu had the most influence on CIELAB color value, while malvidin 3-O-glucoside (Mv3-glu had the least. The color values of various monomeric anthocyanins were influenced by their structures, substituents on the B-ring, acyl groups on the glucoside and the molecular steric structure. This work develops a statistical method for evaluating correlation between wine color and monomeric anthocyanins, and also provides a basis for elucidating the effect of intramolecular copigmentation on wine coloring.

  4. Oxidative acylation using thioacids

    Liu, R.; Orgel, L. E.

    1997-01-01

    Several important prebiotic reactions, including the coupling of amino acids into polypeptides by the formation of amide linkages, involve acylation. Theae reactions present a challenge to the understanding of prebiotic synthesis. Condensation reactions relying on dehydrating agents are either inefficient in aqueous solution or require strongly acidic conditions and high temperatures. Activated amino acids such as thioester derivatives have therefore been suggested as likely substrates for prebiotic peptide synthesis. Here we propose a closely related route to amide bond formation involving oxidative acylation by thioacids. We find that phenylalanine, leucine and phenylphosphate are acylated efficiently in aqueous solution by thioacetic acid and an oxidizing agent. From a prebiotic point of view, oxidative acylation has the advantage of proceeding efficiently in solution and under mild conditions. We anticipate that oxidative acylation should prove to be a general method for activating carboxylic acids, including amino acids.

  5. Anthocyanins as Functional Food Colors

    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.

  6. Effect of Three Training Systems on Grapes in a Wet Region of China: Yield, Incidence of Disease and Anthocyanin Compositions of Vitis vinifera cv. Cabernet Sauvignon.

    Liu, Mei-Ying; Chi, Ming; Tang, Yong-Hong; Song, Chang-Zheng; Xi, Zhu-Mei; Zhang, Zhen-Wen

    2015-01-01

    Grapevine training systems determine the suitability for grape varieties in a specific growing region. We evaluated the influence of three training systems, Single Guyot (SG), Spur-pruned Vertical Shoot-Positioned (VSP), and Four-Arm Kniffin (4AK), on the performance of grapes and vines of Vitis vinifera L. cv. Cabernet Sauvignon in the 2012 and 2013 growing seasons in a wet region of central China. 4AK was the most productive system in comparison to SG and VSP. SG and VSP had lower disease infections of leaves and berries, especially in the mid- and final stage of berry ripening. Three training systems had no impact on berry maturity. PLS-DA (Partial Least Squares-Discriminant) analysis showed that the relatively dry vintage could well discriminate three training systems, but the wet vintage was not. A wet vintage of 2013 had more accumulation of 3'5'-substituted and acylated anthocyanins, including malvidin-3-O-(6-O-acetyl)-glucoside, malvidin-3-O-glucoside, and petunidin-3-O-(cis-6-O-coumaryl)-glucoside, etc. With regard to the effect of training systems, 4AK grapes had the lowest concentrations of total anthocyanins and individual anthocyanins, SG and VSP differed according to the different vintages, and showed highest concentration of total individual anthocyanins in 2012 and 2013, respectively. Generally, VSP benefited the most, contributing to significantly highest levels of total individual anthocyanins, and major anthocyanin, including malvidin-3-O-glucoside and malvidin-3-O-(6-O-acetyl)-glucoside, and the grapes obtained from VSP presented significantly highest proportion of 3'5'-substituted anthocyanins. With regard to the ratios of 3'5'/3'-substituted, methoxylated/non-methoxylated and acylated/non-acylated anthocyanins, the significantly higher levels were also shown in VSP system. In summary, VSP was the best training system for Cabernet Sauvignon to accumulate relatively stable individual anthocyanins in this wet region of China and potentially in

  7. Selection of anthocyanin-accumulating potato (Solanum tuberosum L.) cell lines from calli derived from seedlings produced by gamma-irradiated seeds

    Callus cell lines of potato (Solanum tuberosum L. cv. Zarevo) were obtained from seedlings germinated from gamma-irradiated seeds (200 Gy). Some of these cell lines produce red-violet pigments which were identified as acylated anthocyanins. The major anthocyanin was determined to be peonidin 3-O-[6-O-(4-O-E-p-coumaroyl-rhamnosyl)-glucoside]-5-O-glucoside (“peonanin”). Single cell-derived protoclones from non-pigmented protoplasts sometimes also gave rise to pigmented cell clusters thus indicating that the changes in the expression of the anthocyanin pathway can also occur after the stage of initial callus induction

  8. KARAKTERISTIK WARNA DAN AKTIVITAS ANTIOKSIDAN ANTOSIANIN UBI JALAR UNGU [Color Characteristics and Antioxidant Activity of Anthocyanin Extract from Purple Sweet Potato

    Ai Mahmudatussa’adah1,2*

    2014-12-01

    Full Text Available Anthocyanin is a natural pigment that produces a range of colors, varying from red, purple, blue to yellow. The stability of the anthocyanin color is affected by pH, temperature, and light. Purple sweet potato is rich in anthocyanin, particularly a stable acylated anthocyanin. This research was conducted to study the effect of pH on color and antioxidative activity of anthocyanin extracted from purple sweet potatoes, harvested from Cilembu-Sumedang, Banjaran-Bandung, and Pakembangan-Kuningan. The experiments applied a completely randomized design with two replicates, analyzed in triplo. The results showed that the total number of monomeric anthocyanin in purple sweet potato harvested from Cilembu (3.78±0.08 mg cyanidin-3-glucoside/g dry weight, dw was higher than that of Banjaran (3.18±0.01 mg/g and Pakembangan (2.25±0.01 mg/g. The color of purple sweet potato anthocyanin extract was pH dependent. The color changed from red to faded red, purple, blue, green, and yellow as the pH increased from 1 to 14. The content of anthocyanins from three locations of purple sweet potatoes differed from each other (p<0.05. Radical scavenging activity and reducing power of purple sweet potato anthocyanins extracted at pH 1 was higher than that at pH 4.5 and pH 7.

  9. Acyl-acyl carrier protein: Lysomonogalactosyldiacylglycerol acyl transferase in Anabaena variabilis

    Monogalactosyldiacylglycerol was produced when membranes isolated from the cyanobacterium, Anabaena variabilis, and washed free of soluble endogenous constituents, were incubated with (14C)acyl-acyl carrier protein. This enzymatic synthesis of monogalactosyldiacylglycerol localized in the membranes was not dependent on any added cofactors, such as ATP, coenzyme A, and dithiothreitol. Palmitoyl-, stearoyl-, and oleoyl-acyl carrier proteins were approximately equally active as substrates with Km of 0.37, 0.36, and 0.23 μM, respectively. The (14C)acyl group was exclusively transferred to the sn-1 hydroxyl of the glycerol backbone of monogalactosyldiacylglycerol as demonstrated by hydrolysis of all incorporated acyl groups by the lipase from Rhizopus arrhizus delamar. Using a double labelled (14C)acyl-(14C)acyl carrier protein, this enzyme catalyzed the direct transfer of the acyl group from acyl-acyl carrier protein to an endogenous lysomonogalactosyldiacylglycerol to form monogalactosyldiacylglycerol. The transfer reaction mechanism was also confirmed by the increased activity with the addition of the lysomonogalactosyldiacylglycerol suspension. A specific galactolipid acyl hydrolase activity was released into the soluble protein fraction when the membranes of Anabaena variabilis were treated with 2% Triton X-100. The positional specificity of this acyl hydrolase was demonstrated to be similar to that of Rhizopus lipase, i.e. only the acyl group at the sn-1 position was hydrolyzed. The acyl hydrolase which was also localized in the membrane fraction of Anabaena variabilis was presumably responsible for producing endogenous lysomonogalactosyldiacylglycerol used by the acyltransferase

  10. Anthocyanin stability: a chemometrical approach

    Cabrita, Luís; Fossen, Torgils; Flåten, Geir R.; Andersen, Øyvind M

    2002-01-01

    The stability of cyanidin 3-glucoside towards five different factors (pH, anthocyanin concentration, sodium chloride concentration, ascorbic acid concentration, Oxygen) was studied during 60 days storage at room temperature using a 2^4-1 reduced factorial design. The influence of each individual parameter on anthocyanin stability was found to vary as a function of time. Sodium chloride and ascorbic acid were, respectively, the variables most contributing to and against antho...

  11. Enzymatic acylation of starch.

    Alissandratos, Apostolos; Halling, Peter J

    2012-07-01

    Starch a cheap, abundant and renewable natural material has been chemically modified for many years. The popular modification acylation has been used to adjust rheological properties as well as deliver polymers with internal plasticizers and other potential uses. However the harsh reaction conditions required to produce these esters may limit their use, especially in sensitive applications (foods, pharmaceuticals, etc.). The use of enzymes to catalyse acylation may provide a suitable alternative due to high selectivities and mild reaction conditions. Traditional hydrolase-catalysed synthesis in non-aqueous apolar media is hard due to lack of polysaccharide solubility. However, acylated starch derivatives have recently been successfully produced in other non-conventional systems: (a) surfactant-solubilised subtilisin and suspended amylose in organic media; (b) starch nanoparticles dispersed in organic medium with immobilised lipase; (c) aqueous starch gels with lipase and dispersed fatty acids. We attempt a systematic review that draws parallels between the seemingly unrelated approaches described. PMID:22138593

  12. Genetical and biochemical evidence that the hydroxylation pattern of the anthocyanin B-ring in Silene dioica is determined at the p-coumaroyl-coenzyme a stage

    Kamsteeg, J.; Brederode, J. van; Nigtevecht, G. van

    1980-01-01

    In petals of Silene dioica, gene P controls the 3′-hydroxylation of the anthocyanin B-ring and the hydroxylation pattern of the hydroxycinnamoyl acyl group bound to the 4″'-hydroxyl group of rhamnose of anthocyanidin 3-rhamnosyl(1→6)glucoside-5-glucoside. In this paper, experiments are presented whi

  13. Anthocyanins facilitate tungsten accumulation in Brassica

    Hale, K.L.

    2002-11-01

    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.

  14. Effects of Climatic Conditions and Soil Properties on Cabernet Sauvignon Berry Growth and Anthocyanin Profiles

    Guo Cheng

    2014-09-01

    Full Text Available 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

  15. Mulberry anthocyanin biotransformation by intestinal probiotics.

    Cheng, Jing-Rong; Liu, Xue-Ming; Chen, Zhi-Yi; Zhang, You-Sheng; Zhang, Ye-Hui

    2016-12-15

    This study was designed to evaluate mulberry anthocyanins bioconversion traits for intestinal probiotics. Five intestinal beneficial bacteria were incubated with mulberry anthocyanins under anaerobic conditions at 37°C, and bacterial β-glucosidase activity and anthocyanin level were determined. Results demonstrated that all strains could convert mulberry anthocyanins to some extent. With high β-glucosidase production capacity, Streptococcus thermophiles GIM 1.321 and Lactobacillus plantarum GIM 1.35 degraded mulberry anthocyanins by 46.17% and 43.62%, respectively. Mulberry anthocyanins were mainly biotransformed to chlorogenic acid, crypto-chlorogenic acid, caffeic acid, and ferulic acid during the anaerobic process. Non-enzymatic deglycosylation of anthocyanins also occurred and approximately 19.42% of the anthocyanins were degraded within 48h by this method. PMID:27451240

  16. Feasibility study of FT-MIR spectroscopy and PLS-R for the fast determination of anthocyanins in wine.

    Romera-Fernández, M; Berrueta, L A; Garmón-Lobato, S; Gallo, B; Vicente, F; Moreda, J M

    2012-01-15

    The feasibility of using Fourier Transform Mid-Infrared Spectroscopy (FT-MIR) combined with Partial Least Squares Regression (PLS-R) for the determination of 12 anthocyanins (3-O-glucosides of delphinidin, cyanidin, petunidin, peonidin and malvidin, as well as acetic acid esters and p-coumaric acid esters of petunidin, peonidin and malvidin and caffeic acid ester of malvidin) and three sums (sum of non-acylated anthocyanins, sum of acetylated anthocyanins and sum of coumaroylated anthocyanins), in red wines has been tested. Reference values of anthocyanin concentrations by reverse-phase High Performance Liquid Chromatography with Diode Array Detection (HPLC-DAD) were used to calibrate the models. A Principal Component Analysis (PCA) was applied to these reference values and a differentiation of wine samples by wine type (young wines of 2005, young wines of 2004 and crianza and reserva wines) has been possible. A calibration model using PLS-R was built with 153 samples of Rioja wines and the prediction of the anthocyanin concentrations using this model was evaluated by internal and external validation sample sets. Most of the anthocyanins and their sums have been predicted with a Standard Error of Prediction (SEP) of 15-30% for young wines recently bottled. However, for young wines after one year of being bottled, and for crianza and reserva wines, these errors were unacceptable. The obtained results suggest that the model built for FT-IR instrument calibration is a useful tool for a quick determination of the anthocyanin content of young wines of the current vintage, but a careful robust external validated calibration of the technique is necessary in order to maintain the prediction errors within controlled limits. PMID:22265503

  17. Anthocyanins, colour and antioxidant properties of eggplant (Solanum melongena L.) and violet pepper (Capsicum annuum L.) peel extracts.

    Sadilova, Eva; Stintzing, Florian C; Carle, Reinhold

    2006-01-01

    Acetone extracts from eggplant (Solanum melongena L.) and violet pepper (Capsicum annuum L.) peels both belonging to the Solanaceae plant family were characterized with respect to their anthocyanin profiles, colour qualities and antioxidant capacities. According to HPLC-DAD-MS3 analyses the major anthocyanin in eggplant was delphinidin-3-rutinoside, while the predominant pigment in violet pepper was assigned to delphinidin-3-trans-coumaroylrutinoside-5-glucoside. Since virtually all anthocyanins were delphinidin-based, the effect of acylation and glycosylation patterns on colour stability and antioxidant capacity could be assessed. Application of two in vitro-assays for antioxidant capacity assessment revealed that eggplant generally exhibited higher values compared to violet pepper which was ascribed to 3,5-diglycosylated structures predominating in the latter. The higher extent of acylation in violet pepper was reflected by a more purplish colour shade of the extracts, but did not translate into a higher stability against fading which again was attributed to additional glycosyl substitution at C5. These findings support the relevance of structure-related activities of anthocyanins both for understanding food colour and their particular nutritional value. PMID:16989312

  18. Anthocyanin biosynthetic genes in Brassica rapa

    Guo, Ning; Cheng, Feng; Wu, Jian; Liu, Bo; Zheng, Shuning; Liang, Jianli; Wang, Xiaowu

    2014-01-01

    Background 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. Results In total, we identified 73 genes in...

  19. Anthocyanins from pomegranate (Punica granatum L.)

    Cabrita, Luís; Neves, Higuinaldo Chaves das

    2002-01-01

    The anthocyanin contents in the fruits from three cultivars of Punica granatum L. (asseria, mollar and negral) was studied. Six anthocyanins were isolated from the red seeds of pomegranate fruits using a combination of Sephadex LH-20 column chromatography and reverse-phase semi-preparative HPLC. On the basis of chromatographic and spectroscopic techniques, they were identified as the 3-monoglucosides and 3,5-diglucosides of delphinidin, cyanidin and pelargonidin. Total anthocyanin content in...

  20. Anthocyanins of Hibiscus sabdiffera calyces from Sudan.

    Cahliková, Lucie; Ali, Badreldin H; Havliková, Lucie; Ločárek, Mirek; Siatka, Tomáš; Opletal, Lubomir; Blunden, Gerald

    2015-01-01

    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. PMID:25920224

  1. Effect of Three Training Systems on Grapes in a Wet Region of China: Yield, Incidence of Disease and Anthocyanin Compositions of Vitis vinifera cv. Cabernet Sauvignon

    Mei-Ying Liu

    2015-10-01

    Full Text Available Grapevine training systems determine the suitability for grape varieties in a specific growing region. We evaluated the influence of three training systems, Single Guyot (SG, Spur-pruned Vertical Shoot-Positioned (VSP, and Four-Arm Kniffin (4AK, on the performance of grapes and vines of Vitis vinifera L. cv. Cabernet Sauvignon in the 2012 and 2013 growing seasons in a wet region of central China. 4AK was the most productive system in comparison to SG and VSP. SG and VSP had lower disease infections of leaves and berries, especially in the mid- and final stage of berry ripening. Three training systems had no impact on berry maturity. PLS-DA (Partial Least Squares-Discriminant analysis showed that the relatively dry vintage could well discriminate three training systems, but the wet vintage was not. A wet vintage of 2013 had more accumulation of 3′5′-substituted and acylated anthocyanins, including malvidin-3-O-(6-O-acetyl-glucoside, malvidin-3-O-glucoside, and petunidin-3-O-(cis-6-O-coumaryl-glucoside, etc. With regard to the effect of training systems, 4AK grapes had the lowest concentrations of total anthocyanins and individual anthocyanins, SG and VSP differed according to the different vintages, and showed highest concentration of total individual anthocyanins in 2012 and 2013, respectively. Generally, VSP benefited the most, contributing to significantly highest levels of total individual anthocyanins, and major anthocyanin, including malvidin-3-O-glucoside and malvidin-3-O-(6-O-acetyl-glucoside, and the grapes obtained from VSP presented significantly highest proportion of 3′5′-substituted anthocyanins. With regard to the ratios of 3′5′/3′-substituted, methoxylated/non-methoxylated and acylated/non-acylated anthocyanins, the significantly higher levels were also shown in VSP system. In summary, VSP was the best training system for Cabernet Sauvignon to accumulate relatively stable individual anthocyanins in this wet region of

  2. Acylated delphinidin glycosides from violet and violet-blue flowers of Clematis cultivars and their coloration.

    Sakaguchi, Keisuke; Kitajima, Junichi; Iwashina, Tsukasa

    2013-11-01

    Three new acylated delphinidin glycosides, delphinidin 3-O-beta-[(2"-trans-caffeoylglucopyranosyl)-(1 --> 2)-(6"-succinylgalactopyranoside)]-7-O-beta-glucopyranoside (1), delphinidin 3-O-beta-[(2"-trans-caffeoylglucopyranosyl)-(1 --> 2)-(6"-trans-caffeoyl-tartaroyl-malonylgalactopyranoside)]-7-O-beta-glucopyranoside (2), and delphinidin 3-O-beta-[(2"-trans-caffeoylglucopyranosyl)-(1 --> 2)-(6"-trans-caffeoyl-tartaroyl-malonylgalactopyranoside)]-3'-O-beta-glucuronopyranoside (3), were isolated from the violet and violet-blue sepals of Clematis cultivars 'Jackmanii Superba' and 'Fujimusume'. The chemical structures of the isolated anthocyanins were determined by LC-MS, characterization of hydrolyzates, and UV, 1H and 13C NMR spectroscopy. The visible absorption spectra of these anthocyanins were compared with those of fresh sepals and crude extracts in pH 5.1 buffer solution. In addition, the co-pigment effect with some kaempferol glycosides and caffeoylglucose was examined. PMID:24427942

  3. Influence of Genetic Background on Anthocyanin and Copigment Composition and Behavior during Thermoalkaline Processing of Maize.

    Collison, Amy; Yang, Liyi; Dykes, Linda; Murray, Seth; Awika, Joseph M

    2015-06-10

    Visual color is a primary quality factor for foods purchase; identifying factors that influence in situ color quality of pigmented maize during processing is important. Twenty-four genetically distinct pigmented maize hybrids (red/blue, blue, red, and purple) were used to investigate the effect of pigment and copigment composition on color stability during nixtamalization and tortilla chip processing. The red/blue and blue samples generally contained higher proportions of acylated anthocyanins (mainly cyanidin-3-(6″-malonylglucoside)) than the red and purple color classes. Phenolic amides were the major extractable copigments in all samples (450-764 μg/g), with red samples containing the most putrescines and blue samples containing the most spermidines. Even though samples with higher proportions of acylated anthocyanins retained more pigments during processing, this did not relate to final product color quality. In general, the red/blue samples retained their color quality the best and thus are good candidates for genetic improvement for direct processing into alkalized products. PMID:26010030

  4. High variability in anthocyanin contents between different blackcurrant varieties

    Hellström, Jarkko; Hietaranta, Tarja; Karhu, Saila; Mattila, Pirjo; Tiirikka, Timo; Veteläinen, Merja

    2010-01-01

    The results confirm that blackcurrant is a good source of anthocyanins. However, remarkable variation in the anthocyanin content between varieties is evident. The anthocyanin profile is always dominated by four major anthocyanins, yet some variation appears in their relative proportions. The high anthocyanin content is usually most desirable in the blackcurrant products and this study shows that the choice of variety may have a great impact on it.

  5. Molar absorptivity (ε) and spectral characteristics of cyanidin-based anthocyanins from red cabbage.

    Ahmadiani, Neda; Robbins, Rebecca J; Collins, Thomas M; Giusti, M Monica

    2016-04-15

    Red cabbage extract contains mono and di-acylated cyanidin (Cy) anthocyanins and is often used as food colorants. Our objectives were to determine the molar absorptivity (ε) of different red cabbage Cy-derivatives and to evaluate their spectral behaviors in acidified methanol (MeOH) and buffers pH 1-9. Major red cabbage anthocyanins were isolated using a semi-preparatory HPLC, dried and weighed. Pigments were dissolved in MeOH and diluted with either MeOH (0.1% HCl) or buffers to obtain final concentrations between 5×10(-5) and 1×10(-3) mol/L. Spectra were recorded and ε calculated using Lambert-Beer's law. The ε in acidified MeOH and buffer pH 1 ranged between ~16,000-30,000 and ~13,000-26,000 L/mol cm, respectively. Most pigments showed higher ε in pH 8 than pH 2, and lowest ε between pH 4 and 6. There were bathochromic shifts (81-105 nm) from pH 1 to 8 and hypsochromic shifts from pH 8 to 9 (2-19 nm). Anthocyanins molecular structures and the media were important variables which greatly influenced their ε and spectral behaviors. PMID:26617032

  6. Stability of Anthocyanins from Red Grape Skins under Pressurized Liquid Extraction and Ultrasound-Assisted Extraction Conditions

    Ali Liazid

    2014-12-01

    Full Text Available The stability of anthocyanins from grape skins after applying different extraction techniques has been determined. The following compounds, previously extracted from real samples, were assessed: delphinidin 3-glucoside, cyanidin 3-glucoside, petunidin 3-glucoside, peonidin 3-glucoside, malvidin 3-glucoside, peonidin 3-acetylglucoside, malvidin 3-acetylglucoside, malvidin 3-caffeoylglucoside, petunidin 3-p-coumaroylglucoside and malvidin 3-p-coumaroylglucoside (trans. The techniques used were ultrasound-assisted extraction and pressurized liquid extraction. In ultrasound-assisted extraction, temperatures up to 75 °C can be applied without degradation of the aforementioned compounds. In pressurized liquid extraction the anthocyanins were found to be stable up to 100 °C. The relative stabilities of both the glycosidic and acylated forms were evaluated. Acylated derivatives were more stable than non-acylated forms. The differences between the two groups of compounds became more marked on working at higher temperatures and on using extraction techniques with higher levels of oxygen in the extraction media.

  7. Microwave-assisted extraction of anthocyanin from Chinese bayberry and its effects on anthocyanin stability

    Wenkai DUAN; Jin, Shiping; Guofu ZHAO; SUN, PEILONG

    2015-01-01

    AbstractAnthocyanins are present in high concentrations in Chinese bayberry, Myrica rubra Sieb. & Zucc. Herein, a microwave-assisted extraction was used to extract the anthocyanins from Chinese bayberry. The HPLC chromatogram of the extracts showed that the anthocyanin components were slightly hydrolysed during the extraction process. Further experiments confirmed that microwave irradiation slightly hydrolysed cyanidin-3-O-glucoside to cyanidin, but did not significantly influence the antioxi...

  8. Interplay between anthocyanins and gut microbiota.

    Faria, Ana; Fernandes, Iva; Norberto, Sónia; Mateus, Nuno; Calhau, Conceição

    2014-07-23

    Anthocyanins are naturally occurring compounds abundant in the human diet. Evidence has accumulated regarding the positive association of their intake with healthy biological effects. The microbiota has just been started to be considered as a metabolic organ, hence contributing to the metabolism of phenolic compounds and, consequently, to their bioavailability and the biological effects displayed by them. This review aimed to compile information regarding interaction of anthocyanins with the microbiota, from two perspectives: (i) identification of their colonic metabolites as potential bioactive molecules and (ii) their role as prebiotic agents. These perspectives are key points in anthocyanin metabolomics. Several metabolites have been identified after anthocyanin consumption with potential health benefits, in particular phenolic acids and simple phenols. On the other hand, microbiota modulation is closely related to several physiological impairments, and its modulation has been considered as a possible mechanism by which phenolic compounds may exert their effect. PMID:24915058

  9. Change of anthocyanins content during raspberry extraction

    Vukosavljević Predrag

    2003-01-01

    Full Text Available Change in anthocyanins content under different conditions of extraction enzymatic maceration and heat treatment of two raspberry cultivars (Villamette and Meeker was determined. Experiments were carried out on a laboratory hydraulic extractor. During extraction commercial operating conditions were emulated using a "Bucher" extractor (pressure 180-200 bar 1-3 pulp shakings. A pectin preparation Klerzyme®120, manufactured by DSM France, was used for maceration and depectinization, because it is specific for "sour fruits" with pH below 3.2. At a single-stage maceration, it was applied in the amount of 200-400 g/t, for 1-2 hours at 50oC. In a two-stage maceration and depectinization, the enzyme was added as follows: in the first stage 100-200 g/t for 0.5 - 1 hour at 20oC and in the second stage 4-8 g/hl for 1-2 hours at 200C. Thermal breaks of raspberry pulp were performed at raised temperatures for 2 and 5 min in order to examine the effects of raised temperatures on anthocyanins extraction. The application of heat-enzymatic treatments of the pulp prior to extraction proved to be suitable in both raspberry cultivars. Apart from well-known degrading effects of heat on anthocyanins, the juice obtained by extraction, after enzymatic maceration, has higher anthocyanins content by 30% than the juice obtained without enzymatic maceration. Juice pasteurization, in each stage of processing, produced markedly negative effect on anthocyanins content therefore their content decreases considerably. The forms of anthocyanins that are lost most are those uncolored. In batches subjected to a two -stage enzymatic maceration, despite initial high anthocyanins content, the content of total anthocyanins is reduced after the second pasteurization to the approximate value as that in batches subjected to a single-stage enzymatic maceration.

  10. Anthocyanins influence tannin-cell wall interactions.

    Bautista-Ortín, Ana Belén; Martínez-Hernández, Alejandro; Ruiz-García, Yolanda; Gil-Muñoz, Rocío; Gómez-Plaza, Encarna

    2016-09-01

    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. PMID:27041322

  11. 花色苷的热稳定性及其影响因素研究%Thermal stability and impacting factors of anthocyanins

    董楠; 雷丹丹; 刘嘉; 赵国华

    2012-01-01

    Anthocyanins with physiological function of antioxidant activity,antitumor activity,and so on,are excellent sources of natural plants colorants.Degradation of anthocyanins during the thermal process limits their applications in food industrial.Kinetics and factors of thermal degradation of anthocyanins were reviewed on the basis of referring to a lot of researches home and abroad.Degradation of anthocyanins during the thermal process belongs to first order kinetics,and the influence factors including:pH,pressure,temperature,sugar,flavonoid,ascorbic acid,and acylation degree in anthocyanins.%花色苷是优良的天然植物源色素,同时具备抗氧化、抗肿瘤等重要生理功能。花色苷的热稳定性是影响其在食品工业中应用的主要因素,本文对花色苷的热降解动力学和热降解影响因素进行了综述。花色苷在食品中的热降解动力学均为一级动力学,影响其降解的主要因素包括pH、压强、温度、糖类、黄酮类物质、抗坏血酸类及其自身的酰基化程度。

  12. Preparation and Characterization of Acylated Chitosan

    LI Ming-chun; LIU Chao; XIN Mei-hua; ZHAO Huang; WANG Min; FENG Zhen; SUN Xiao-li

    2005-01-01

    Fully acylated chitosan and N, N-diacyl chitosan were prepared. The products were characterized by elemental analysis, FTIR and 1H NMR. The experimental results indicate that the average degree of acylation depends on the volume ratio of pyridine to chloroform in the reaction medium, the chain length of the acylation agent used, and the molecular weight of chitosan raw materials. The XRD measurements were carried out for pure chitosan, fully acylated chitosan and N, N-diacyl chitosan to verify the crystallinity change caused by the acylation.

  13. RNA SHAPE chemistry with aromatic acylating reagents.

    Nodin, Laura; Noël, Olivier; Chaminade, Françoise; Maskri, Ouerdia; Barbier, Vincent; David, Olivier; Fossé, Philippe; Xie, Juan

    2015-02-01

    As chemical methods for RNA secondary structure determination, SHAPE chemistry (selective 2'-hydroxyl acylation analyzed by primer extension) has been developed to specifically target flexible nucleotides (often unpaired nucleotides) independently to their purine or pyrimidine nature. In order to improve the specificity of acylating reagents towards unpaired nucleotides, we have explored the reactivity of symmetric anhydrides, acyl fluorides, active esters like succinimidyl ester and cyanomethyl esters for 2'-O-acylation reaction. Among the tested compounds, only the acyl fluoride 4 showed a low reactivity (compared to NMIA). However, this study is the first to show that nucleophilic catalysts like DMAP greatly improved the selective 2'-hydroxyl acylation by symmetric anhydrides, acyl fluorides and succinimidyl ester, with the 2-fluorobenzoic anhydride 5 being the most reactive. PMID:25557357

  14. Light-induced vegetative anthocyanin pigmentation in Petunia

    Albert, Nick W.; David H Lewis; Zhang, Huaibi; Irving, Louis J.; Jameson, Paula E; Davies, Kevin M.

    2009-01-01

    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...

  15. Anthocyanins and Their Variation in Red Wines II. Anthocyanin Derived Pigments and Their Color Evolution

    Chang-Qing Duan

    2012-02-01

    Full Text Available 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.

  16. Identification and quantification of anthocyanins in transgenic purple tomato.

    Su, Xiaoyu; Xu, Jianteng; Rhodes, Davina; Shen, Yanting; Song, Weixing; Katz, Benjamin; Tomich, John; Wang, Weiqun

    2016-07-01

    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. PMID:26920283

  17. Expression and mapping of anthocyanin biosynthesis genes in carrot

    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 (...

  18. Anthocyanin content and UVB sensitivity in Brassica rapa

    Three genotypes of rapid-cycling Brassica rapa that differ in anthocyanin content were grown in the presence and absence of elevated levels of shortwave ultraviolet (UBV, 280-325 nm) radiation. After 41 days, UVB exposure reduced leaf length and plant height of all genotypes. Plants with low levels of anthocyanin experienced a reduction in flower number twice as great as in genotypes with normal or elevated levels of anthocyanins; however, the absence of differences in flower production by genotypes with normal and elevated levels of anthocyanins suggests that factors other than anthocyanin pigmentation contribute to UVB responses in this species. (UK)

  19. Anthocyanin content and UVB sensitivity in Brassica rapa

    Klaper, R.; Frankel, S.; Berenbaum, M.R. [Illinois Univ., Urbana, IL (United States)

    1996-06-01

    Three genotypes of rapid-cycling Brassica rapa that differ in anthocyanin content were grown in the presence and absence of elevated levels of shortwave ultraviolet (UBV, 280-325 nm) radiation. After 41 days, UVB exposure reduced leaf length and plant height of all genotypes. Plants with low levels of anthocyanin experienced a reduction in flower number twice as great as in genotypes with normal or elevated levels of anthocyanins; however, the absence of differences in flower production by genotypes with normal and elevated levels of anthocyanins suggests that factors other than anthocyanin pigmentation contribute to UVB responses in this species. (UK).

  20. Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression

    Chang-Qing Duan

    2012-02-01

    Full Text Available 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.

  1. 加工方法对紫甘薯花色苷含量及组成的影响%Effectsof Processing Technique on Anthocyanin Composition and Content of Purple Sweet Potato

    王晰锐; 张超; 马越; 江连洲; 赵晓燕

    2011-01-01

    Objective: Effects of roasting, frying, and steaming treatments on the anthocyanin composition and content of purple sweet potato were evaluated. Methods: The anthocyanin content and compositions of the purple sweet potato was detected by HPLC-MS. Results: Each treatment decreased the anthocyanin content. The anthocyanin residual rate in purple sweet potato treated by frying, steaming, and roasting were 93.7%, 87.1%, and 60.0%, respectively. Moreover, the diacylated anthocyanin showed a stronger stability than the acylated ones. The stability of the caffeoyl anthocyanin was stronger than that of the phydroxybenzoyl anthocyanin. Conclusion: The frying and steaming were effective to hold the anthocyanin content of the purple sweet potato.%目的:研究烤、炸和蒸3种加工方法对紫甘薯花色苷的影响.方法:采用HPLC-MS法测定3种加工方法对紫甘薯花色苷含量及其组成的变化.结果:3种加工方法均可降低紫甘薯花色苷含量,其花色苷残余率:炸薯93.7%,蒸薯87.1%和烤薯60.0%.紫甘薯中双酰化的花色苷稳定性高于单酰化花色苷,咖啡酸酰化的花色苷组分稳定性高于对羟基苯甲酸酰化花色苷.结论:炸和蒸加工方法可有效维持紫甘薯花色苷含量.

  2. Acyl-CoA metabolism and partitioning

    Grevengoed, Trisha J; Klett, Eric L; Coleman, Rosalind A

    2014-01-01

    expression patterns and subcellular locations. Their acyl-CoA products regulate metabolic enzymes and signaling pathways, become oxidized to provide cellular energy, and are incorporated into acylated proteins and complex lipids such as triacylglycerol, phospholipids, and cholesterol esters. Their differing...... metabolic fates are determined by a network of proteins that channel the acyl-CoAs toward or away from specific metabolic pathways and serve as the basis for partitioning. This review evaluates the evidence for acyl-CoA partitioning by reviewing experimental data on proteins that are believed to contribute...

  3. Microwave-assisted extraction of anthocyanin from Chinese bayberry and its effects on anthocyanin stability

    Wenkai DUAN

    2015-09-01

    Full Text Available AbstractAnthocyanins are present in high concentrations in Chinese bayberry, Myrica rubra Sieb. & Zucc. Herein, a microwave-assisted extraction was used to extract the anthocyanins from Chinese bayberry. The HPLC chromatogram of the extracts showed that the anthocyanin components were slightly hydrolysed during the extraction process. Further experiments confirmed that microwave irradiation slightly hydrolysed cyanidin-3-O-glucoside to cyanidin, but did not significantly influence the antioxidant activity of the extracts. Optimized extraction conditions for total anthocyanin content were a solid-to-liquid ratio, extraction temperature, and extraction time of 1:50, 80 °C, and 15 min, respectively. Under these conditions, the anthocyanin content was 2.95 ± 0.08 mg·g−1, and the antioxidant activity yield was 279.96 ± 0.1 μmol.·g−1 Trolox equivalent on a dry weight basis. These results indicated that microwave-assisted extraction was a highly efficient extraction method with reduced processing time. However, under some extraction conditions it could damage the anthocyanins. These results provide an important guide for the application of microwave extraction.

  4. Distinctive Anthocyanin Accumulation Responses to Temperature and Natural UV Radiation of Two Field-Grown Vitis vinifera L. Cultivars

    Ana Fernandes de Oliveira

    2015-01-01

    Full Text Available The responses of two red grape varieties, Bovale Grande (syn. Carignan and Cannonau (syn. Grenache, to temperature and natural UV radiation were studied in a three-years field experiment conducted in Sardinia (Italy, under Mediterranean climate conditions. Vines were covered with plastic films with different transmittances to UV radiation and compared to uncovered controls. Light intensity and spectral composition at the fruit zone were monitored and berry skin temperature was recorded from veraison. Total skin anthocyanin content (TSA and composition indicated positive but inconsistent effects of natural UV light. Elevated temperatures induced alterations to a greater extent, decreasing TSA and increasing the degree of derivatives acylation. In Cannonau total soluble solids increases were not followed by increasing TSA as in Bovale Grande, due to both lower phenolic potential and higher sensitivity to permanence of high temperatures. Multi linear regression analysis tested the effects of different ranges of temperature as source of variation on anthocyanin accumulation patterns. To estimate the thermal time for anthocyanin accumulation, the use of normal heat hours model had benefit from the addition of predictor variables that take into account the permanence of high (>35 °C and low (<15 °C and <17 °C temperatures during ripening.

  5. ANTHOCYANIN (ACN) STABILITY IN CELL CULTURE MEDIA

    Anthocyanins (ACNs) are potential oxygen radical scavengers that have coronary vasoactive and vasoprotective properties. Cell or tissue culture systems have been used to examine the bioactivity and mechanisms of action of ACNs on the vascular system. However, due to their unique chemical structure, ...

  6. Anthocyanins: Do they really prevent obesity?

    Male C57BL6 mice received diets with either 10% of cal. from fat (LF), a high fat diet [45% (HF45) or 60% (HF60) cal. from fat]. In 2 studies these were given with or without: freeze dried powders from whole blueberries (BB), strawberries (SB), black raspberries (BR) or concentrated anthocyanins (AC...

  7. Comparison of Two Methods for Anthocyanin Quantification

    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 ...

  8. Chemistry, Pharmacology and Health Benefits of Anthocyanins.

    Smeriglio, Antonella; Barreca, Davide; Bellocco, Ersilia; Trombetta, Domenico

    2016-08-01

    Anthocyanins are naturally occurring molecules belonging to the flavonoid class characterized by the presence of chromophores. Apart from their well-known antioxidant activity, they show a wide variety of health-promoting properties for human health, ranging from cytoprotective, antimicrobial and antitumour activities to neuroprotective, anti-obesity and lipidomic potential, properties for which anthocyanins have been prescribed as medicines in several countries for thousands of years. Despite this, these phytochemicals have received less attention than other flavonoids, and there is still a gap in the literature, particularly regarding pharmacological and toxicological aspects. Moreover, epidemiological evidence suggests a direct correlation between anthocyanin intake and a lower incidence of chronic and degenerative diseases. In light of this, the aim of this review is to cover the current literature on anthocyanins, their biological in vitro and in vivo effects and their potential therapeutic applications, as well as their bioavailability and pharmacokinetics, all of which are essential to gain a better understanding of their biological effectiveness and potential toxicity. Copyright © 2016 John Wiley & Sons, Ltd. PMID:27221033

  9. Antioxidant capacity of anthocyanins from acerola genotypes

    Vera Lúcia Arroxelas Galvão De Lima

    2011-03-01

    Full Text Available Anthocyanins from 12 acerola genotypes cultivated at the Active Germplasm Bank at Federal Rural University of Pernambuco were isolated for antioxidant potential evaluation. The antioxidant activity and radical scavenging capacity of the anthocyanin isolates were measured according to the β-carotene bleaching method and 1,1-diphenyl-2-picrylhydrazyl (DPPH free radical scavenging assay, respectively. The antioxidant activity varied from 25.58 to 47.04% at 0.2 mg.mL-1, and it was measured using the β-carotene bleaching method. The free radical scavenging capacity increased according to the increase in concentration and reaction time by the DPPH assay. At 16.7 μg.mL-1 concentration and after 5 minutes and 2 hours reaction time, the percentage of scavenged radicals varied from 36.97 to 63.92% and 73.27 to 94.54%, respectively. Therefore, the antioxidant capacity of acerola anthocyanins varied amongst acerola genotypes and methods used. The anthocyanins present in this fruit may supply substantial dietary source of antioxidant which may promote health and produce disease prevention effects.

  10. Grape anthocyanin altered by absolute sunlight exclusion

    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...

  11. Effects of Cerium on Accumulation of Anthocyanins and Expression of Anthocyanin Biosynthetic Genes in Potato Cell Tissue Cultures

    2006-01-01

    The effects of Ce (Ⅳ) on callus growth, anthocyanin content, and expression of anthocyanin biosynthetic genes in callus suspension cultures of Solanum tuberosum cv. Chieftain were studied by the measurement of fresh weight, spectrophotometric assays, and semiquantitative RT-PCR. The results indicate that 0.1 mmol·L-1 Ce (Ⅳ) can promote callus growth, increase the accumulation of anthocyanins, and enhance the expression of five anthocyanin biosynthetic genes (CHS, F3H, F3′5′H, DFR, and 3GT) most efficiently. At high concentrations of 1 mmol·L-1, Ce (Ⅳ) partially inhibits callus growth and at 2 mmol·L-1 eventually lends to cell death. The results show that Ce(Ⅳ) can induce the expression of anthocyanin biosynthetic genes to produce and accumulate anthocyanins and increase the yield of anthocyanins.

  12. Acylated flavone glycosides from Veronica

    Albach, Dirk C.; Grayer, Renée J.; Jensen, Søren Rosendal;

    2003-01-01

    A survey of the flavonoid glycosides of selected taxa in the genus Veronica yielded two new acylated 5,6,7,3',4'-pentahydroxyflavone (6-hydroxyluteolin) glycosides and two rare allose-containing acylated 5,7,8,4'-tetrahydroxyflavone (isoscutellarein) glycosides. The new compounds were isolated from...... Veronica (melittoside and globularifolin) were also isolated from V. intercedens....

  13. Coordinated regulation of biosynthetic and regulatory genes coincides with anthocyanin accumulation in developing eggplant fruit

    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...

  14. Anthocyanin antioxidant activity and partition behavior in whey protein emulsion.

    Viljanen, Kaarina; Kylli, Petri; Hubbermann, Eva-Maria; Schwarz, Karin; Heinonen, Marina

    2005-03-23

    The antioxidant activities of anthocyanins and anthocyanin fractions isolated from blackcurrants, raspberries, and lingonberries were investigated in whey protein-stabilized emulsion. The extent of protein oxidation was measured by determining the loss of tryptophan fluorescence and formation of protein carbonyl compounds and that of lipid oxidation by conjugated diene hydroperoxides and hexanal analyses. The antioxidant activity of berry anthocyanins increased with an increase in concentration. Blackcurrant anthocyanins were the most potent antioxidants toward both protein and lipid oxidation at all concentrations due to the beneficial combination of delphinidin and cyanidin glycosides. Most berry anthocyanins (69.4-72.8%) partitioned into the aqueous phase of the emulsion, thus being located favorably for antioxidant action toward protein oxidation. The presence of the lipid decreased the share of anthocyanin in the aqueous phase. Thus, the structure of food affects the antioxidant activity by influencing the partitioning of the antioxidant. PMID:15769130

  15. Anthocyanins in berries of Maqui (Aristotelia chilensis (Mol.) Stuntz).

    Escribano-Bailón, María Teresa; Alcalde-Eon, Cristina; Muñoz, Orlando; Rivas-Gonzalo, Julián C; Santos-Buelga, Celestino

    2006-01-01

    The anthocyanin composition of berries of Maqui [Aristotelia chilensis (Mol.) Stuntz] was determined by HPLC with photodiode array and MS detection. Eight pigments corresponding to the 3-glucosides, 3,5-diglucosides, 3-sambubiosides and 3-sambubioside-5-glucosides of delphinidin and cyanidin were identified, the principal anthocyanin being delphinidin 3-sambubioside-5-glucoside (34% of total anthocyanins). The average total anthocyanin content was 137.6 +/- 0.4mg/100g of fresh fruit (211.9 +/- 0.6 mg/100g of dry fruit). The relative high anthocyanin content and the important presence of polar polyglycosylated derivatives makes the fruits of A. chilensis an interesting source of anthocyanin extracts for food and pharmaceutical uses. PMID:16454470

  16. Quantification and Purification of Mulberry Anthocyanins with Macroporous Resins

    Xueming Liu

    2004-01-01

    Full Text Available 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.

  17. Sugar-Hormone Cross-Talk in Anthocyanin Biosynthesis

    Das, Prasanta Kumar; Shin, Dong Ho; Choi, Sang-Bong; Park, Youn-Il

    2012-01-01

    Anthocyanins, a class of flavonoids, are recognized for their diverse functions in plant development and beneficial effects on human health. Many of the genes encoding anthocyanin biosynthesis enzymes and the transcription factors that activate or repress them have been identified. Regulatory proteins that control anthocyanin biosynthesis by regulating the expression of different structural genes at the transcriptional and post-transcriptional levels are differentially modulated by environmen...

  18. New insights into regulation of anthocyanin biosynthesis in fruits

    Jaakola, Laura

    2013-01-01

    Anthocyanins are important health-promoting pigments that make a major contribution to the quality of fruits. The biosynthetic pathway leading to anthocyanins is well known and the key regulatory genes controlling the pathway have been isolated in many species. Recently, a considerable amount of new information has been gathered on the developmental and environmental regulation of anthocyanin biosynthesis in fruits, specifically the impact of regulation through light. New discoveries have beg...

  19. Cytokinins Enhance Sugar-Induced Anthocyanin Biosynthesis in Arabidopsis

    Das, Prasanta Kumar; Shin, Dong Ho; Choi, Sang-Bong; Yoo, Sang-Dong; Choi, Giltsu; Park, Youn-II

    2012-01-01

    In higher plants, the regulation of anthocyanin synthesis by various factors including light, sugars and hormones is mediated by numerous regulatory factors acting at the transcriptional level. Here, the association between sucrose and the plant hormone, cytokinin, in the presence of light was investigated to elucidate cytokinin signaling cascades leading to the transcriptional activation of anthocyanin biosynthesis genes in Arabidopsis seedlings. We showed that cytokinin enhances anthocyanin...

  20. CHARACTERIZATION OF MALAYSIAN WILD BANANAS BASED ON ANTHOCYANINS

    MUHAMMAD ASIF JAVED; MAK CHAI; ROFINA YASMIN OTHMAN

    2001-01-01

    The male buds of 16 Musa species (Musaceae) populations were investigated by HPLC for the occurrence of anthocyanins. The investigation was based on the presence of 6 anthocyanins. The 16 Musa samples could be classified into three distinct species i.e. Musa acuminata, Musa violascens and Musa balbisiana. Musa acuminata could be divided into two subspecies : malaccensis (lowland) and tmncata (highland) according to their constituents and content of major anthocyanins. No variation was ob...

  1. ANTHOCYANINS OF SOME HAWTHORN SPECIES (CRATAEGUS L., ROSACEAE) FRUITS

    Виктор Иванович Дейнека; Сергей Леонидович Макаревич; Людмила Александровна Дейнека; Геннадий Афанасьевич Фирсов; Владимир Николаевич Сорокопудов; М Ю Третьяков; Сергей Александрович Бакшутов

    2014-01-01

    Anthocyanins of two hawthorn species fruits: C. chlorosarca Maxim. and C. pentagyna Waldst. et Kit., were investigated by HPLC-DAD-ESI-MS method. Cyanidin-3-galactoside, cyanidine-3-glucoside, cyanidine-3-arabinoside and cyanidine-3-xiloside were found. Overall anthocyanins accumulation was the highest in the case of C. chlorosarca fruits: 0.460÷0.620 g per 100 g of fresh fruits as cyanidine-3-glucoside chloride equivalent. It has been found that according to anthocyanins accumulation as well...

  2. Canna indica flower: New source of anthocyanins.

    Srivastava, Jyoti; Vankar, Padma S

    2010-12-01

    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. PMID:20926305

  3. Change of anthocyanins content during raspberry extraction

    Vukosavljević Predrag; Bukvić Branka; Janković Miodrag 1; Mašović Snežana

    2003-01-01

    Change in anthocyanins content under different conditions of extraction enzymatic maceration and heat treatment of two raspberry cultivars (Villamette and Meeker) was determined. Experiments were carried out on a laboratory hydraulic extractor. During extraction commercial operating conditions were emulated using a "Bucher" extractor (pressure 180-200 bar 1-3 pulp shakings). A pectin preparation Klerzyme®120, manufactured by DSM France, was used for maceration and depectinization, because it ...

  4. Antioxidant activity of anthocyanins from quixabeira (Sideroxylon obtusifolium) fruits

    F.J. FIGUEIREDO; V. L. A. G. LIMA

    2015-01-01

    ABSTRACT The fruits of Sideroxylon obtusifolium T.D. Penn. are small berries which have dark purple skin color at maturity due the anthocyanins presence. Therefore, the aim of this research was to evaluate the antioxidant activity of anthocyanins from mature fruits which were obtained at a semi-arid region of Paraiba/BR. In addition, the total anthocyanins content was measured by the pH differential method. The anthocyanins were purified by solid-phase extraction (SPE) using C18 Sep-Pak cartr...

  5. Acyl-coenzyme A organizes laterally in membranes and is recognized specifically by acyl-coenzyme A binding protein

    Cohen Simonsen, A; Bernchou Jensen, U; Færgeman, Nils J.; Knudsen, J; Mouritsen, O G

    Long chain acyl-coenzyme A (acyl-CoA) is a biochemically important amphiphilic molecule that is known to partition strongly into membranes by insertion of the acyl chain. At present, microscopically resolved evidence is lacking on how acyl-CoA influences and organizes laterally in membranes. By a...

  6. Fatty acyl-CoA reductase

    Reiser, Steven E.; Somerville, Chris R.

    1998-12-01

    The present invention relates to bacterial enzymes, in particular to an acyl-CoA reductase and a gene encoding an acyl-CoA reductase, the amino acid and nucleic acid sequences corresponding to the reductase polypeptide and gene, respectively, and to methods of obtaining such enzymes, amino acid sequences and nucleic acid sequences. The invention also relates to the use of such sequences to provide transgenic host cells capable of producing fatty alcohols and fatty aldehydes.

  7. Adsorption behavior of natural anthocyanin dye on mesoporous silica

    Kohno, Yoshiumi; Haga, Eriko; Yoda, Keiko; Shibata, Masashi; Fukuhara, Choji; Tomita, Yasumasa; Maeda, Yasuhisa; Kobayashi, Kenkichiro

    2014-01-01

    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.

  8. Biosynthesis of Anthocyanins and Their Regulation in Colored Grapes

    Guo-Liang Yan

    2010-12-01

    Full Text Available Anthocyanins, synthesized via the flavonoid pathway, are a class of crucial phenolic compounds which are fundamentally responsible for the red color of grapes and wines. As the most important natural colorants in grapes and their products, anthocyanins are also widely studied for their numerous beneficial effects on human health. In recent years, the biosynthetic pathway of anthocyanins in grapes has been thoroughly investigated. Their intracellular transportation and accumulation have also been further clarified. Additionally, the genetic mechanism regulating their biosynthesis and the phytohormone influences on them are better understood. Furthermore, due to their importance in the quality of wine grapes, the effects of the environmental factors and viticulture practices on anthocyanin accumulation are being investigated increasingly. The present paper summarizes both the basic information and the most recent advances in the study of the anthocyanin biosynthesis in red grapes, emphasizing their gene structure, the transcriptional factors and the diverse exterior regulation factors.

  9. CHARACTERIZATION OF MALAYSIAN WILD BANANAS BASED ON ANTHOCYANINS

    MUHAMMAD ASIF JAVED

    2001-01-01

    Full Text Available The male buds of 16 Musa species (Musaceae populations were investigated by HPLC for the occurrence of anthocyanins. The investigation was based on the presence of 6 anthocyanins. The 16 Musa samples could be classified into three distinct species i.e. Musa acuminata, Musa violascens and Musa balbisiana. Musa acuminata could be divided into two subspecies : malaccensis (lowland and tmncata (highland according to their constituents and content of major anthocyanins. No variation was observed in the composition of the anthocyanins of Kedah type ssp. siamea and Selangor types ssp. malaccensis. The classification of M. acuminata into two subspecies based on anthocyanin data further supported the current taxonomic grouping of the species.

  10. Stability and bioaccessibility of anthocyanins in bakery products enriched with anthocyanins.

    Karakaya, Sibel; Simsek, Sebnem; Eker, Alper Tolga; Pineda-Vadillo, Carlos; Dupont, Didier; Perez, Beatriz; Viadel, Blanca; Sanz-Buenhombre, Marisa; Rodriguez, Alberto Guadarrama; Kertész, Zsófia; Hegyi, Adrienn; Bordoni, Alessandra; El, Sedef Nehir

    2016-08-10

    Anthocyanins, water soluble polyphenols, have been associated with several beneficial health effects. The aim of this study was to determine how the baking process and food matrix affect anthocyanin stability and bioaccessibility in bakery products in order to develop functional foods. Three well known regularly consumed bakery products (buns, breadsticks and biscuits) were enriched with anthocyanin (AC) isolated from grape skin alone or in combination with docosahexaenoic acid (AC + DHA) to reveal knowledge on AC as active ingredients in real food systems rather than pure compounds. Anthocyanin amounts added to the formulations of buns, breadsticks and biscuits were 34 mg per 100 g, 40 mg per 100 g and 37 mg per 100 g, respectively. The effect of processing, storage and the food matrix on AC stability and bioaccessibility was investigated. In addition, the sensory properties of bakery products were evaluated. Breadsticks enriched with AC and AC + DHA received the lowest scores in the pre-screening sensory test. Therefore breadsticks were excluded from further analysis. AC retentions, which were monitored by determination of malvidin 3-O-glucoside, in the bun and biscuit after baking were 95.9% (13.6 mg per 100 g) and 98.6% (15.2 mg per 100 g), respectively. Biscuits and buns enriched only with AC showed significantly higher anthocyanin bioaccessibilities (57.26% and 57.30%, respectively) than the same ones enriched with AC + DHA. AC stability in enriched products stored for 21 days was significantly lower than in products stored for 7 days (p < 0.05). However, this loss can be accepted as negligible since more than 70% of AC was retained in all the products. PMID:27415853

  11. Development of Table and Raisin Grapes With High Anthocyanins Using a Leaf Disk Assay.

    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 ...

  12. Antioxidant activity of anthocyanins from quixabeira (Sideroxylon obtusifolium fruits

    F.J. FIGUEIREDO

    2015-09-01

    Full Text Available ABSTRACT The fruits of Sideroxylon obtusifolium T.D. Penn. are small berries which have dark purple skin color at maturity due the anthocyanins presence. Therefore, the aim of this research was to evaluate the antioxidant activity of anthocyanins from mature fruits which were obtained at a semi-arid region of Paraiba/BR. In addition, the total anthocyanins content was measured by the pH differential method. The anthocyanins were purified by solid-phase extraction (SPE using C18 Sep-Pak cartridges and submitted to antioxidant activity determined by scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH·. The butylated hydroxytoluene (BHT was the positive control and the results were expressed as DPPH· scavenging activity (%. Anthocyanins content were higher in the husks (236.15 mg cyanidin-3-glucoside 100g-1 fw than in the pulp (30.49 mg cyanidin-3-glucoside 100g-1 fw. The results showed that the potential free radical scavenging grew with the increase of concentration used and the reaction time. The ability of the anthocyanins in scavenging the free radical was statistically greater than the BHT one. The anthocyanins which were present in this fruit may supply substantial dietary source of antioxidant that may promote health and produce disease prevention effects or that could be applied in food industry as a good source of natural pigments

  13. Role of acylCoA binding protein in acylCoA transport, metabolism and cell signaling

    Knudsen, J; Jensen, M V; Hansen, J K; Færgeman, Nils J.; Neergaard, T B; Gaigg, B

    Long chain acylCoA esters (LCAs) act both as substrates and intermediates in intermediary metabolism and as regulators in various intracellular functions. AcylCoA binding protein (ACBP) binds LCAs with high affinity and is believed to play an important role in intracellular acylCoA transport and ......) [4]. Additional factors affecting the concentration of free LCA include feed back inhibition of the acylCoA synthetase [5], binding to acylCoA receptors (LCA-regulated molecules and enzymes), binding to membranes and the activity of acylCoA hydrolases [6]....

  14. ANTHOCYANINS OF SOME HAWTHORN SPECIES (CRATAEGUS L., ROSACEAE FRUITS

    Виктор Иванович Дейнека

    2014-09-01

    Full Text Available Anthocyanins of two hawthorn species fruits: C. chlorosarca Maxim. and C. pentagyna Waldst. et Kit., were investigated by HPLC-DAD-ESI-MS method. Cyanidin-3-galactoside, cyanidine-3-glucoside, cyanidine-3-arabinoside and cyanidine-3-xiloside were found. Overall anthocyanins accumulation was the highest in the case of C. chlorosarca fruits: 0.460÷0.620 g per 100 g of fresh fruits as cyanidine-3-glucoside chloride equivalent. It has been found that according to anthocyanins accumulation as well as to the antioxidant activity C. chlorosarca fruits are rather comparable to dried hibiscus subdariffa calyces and may be used for another tea preparation at some acidification.

  15. EFFECT OF ANTHOCYANIN FRACTION ON CISPLATIN-INDUCED NEPHROTOXICITY

    Adikay Sreedevi; Belide Pavani

    2012-01-01

    Present study was designed to evaluate the effect of anthocyanin fraction of Syzygium cumini on cisplatin-induced nephrotoxicity in male Albino rats. Anthocyanin fraction was administered by gastric intubation at two dose levels. Animals were divided into 5 groups. Group I animals received vehicle. On day 1, Group II animals received cisplatin (6 mg/kg, i,p., single dose). Group III (7.5mg/kg) and IV (15mg/kg) received anthocyanin fraction respectively at 1 hr before, 24 hr and 48 hr after ci...

  16. Engineering the anthocyanin regulatory complex of strawberry (Fragaria vesca)

    Lin-Wang, Kui; McGhie, Tony K.; Wang, Mindy; Liu, Yuhui; Warren, Benjamin; Storey, Roy; Espley, Richard V; Allan, Andrew C.

    2014-01-01

    The woodland strawberry, Fragaria vesca is a model fruit for a number of rosaceous crops. We have engineered altered concentrations of anthocyanin in F. vesca, to determine the impact on plant growth and fruit quality. Anthocyanin concentrations were significantly increased by over-expression or decreased by knock-down of the R2R3 MYB activator, MYB10. In contrast, a potential bHLH partner for MYB10 (bHLH33) did not affect the anthocyanin pathway when knocked down using RNAi constructs. Metab...

  17. Simultaneous Analysis of Anthocyanin and Non-Anthocyanin Flavonoid in Various Tissues of Different Lotus (Nelumbo) Cultivars by HPLC-DAD-ESI-MSn

    Sha Chen; Yue Xiang; Jiao Deng; Yanling Liu; Shaohua Li

    2013-01-01

    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 gr...

  18. Minimizing acylation of peptides in PLGA microspheres

    Zhang, Ying; Schwendeman, Steven P.

    2012-01-01

    The main objective of this study was to characterize and find mechanisms to prevent acylation of therapeutic peptides encapsulated in glucose-star poly(D,L-lactic-co-glycolic acid) (PLGA) microspheres. The effect of addition of divalent cation salts CaCl2, MnCl2 as well as carboxymethyl chitosan (CMCS) on inhibition of acylation of octreotide (Oct), salmon calcitonin (sCT), and human parathyroid hormone (hPTH) was evaluated. Peptide content and integrity inside the degrading microspheres was ...

  19. Acyl silicates and acyl aluminates as activated intermediates in peptide formation on clays

    White, D. H.; Kennedy, R. M.; Macklin, J.

    1984-01-01

    Glycine reacts with heating on dried clays and other minerals to give peptides in much better yield than in the absence of mineral. This reaction was proposed to occur by way of an activated intermediate such as an acyl silicate or acyl aluminate analogous to acyl phosphates involved in several biochemical reactions including peptide bond synthesis. The proposed mechanism has been confirmed by trapping the intermediate, as well as by direct spectroscopic observation of a related intermediate. The reaction of amino acids on periodically dried mineral surfaces represents a widespead, geologically realistic setting for prebiotic peptide formation via in situ activation.

  20. Major anthocyanins from purple asparagus (Asparagus officinalis).

    Sakaguchi, Yumi; Ozaki, Yukio; Miyajima, Ikuo; Yamaguchi, Masaatsu; Fukui, Yuko; Iwasa, Keiko; Motoki, Satoru; Suzuki, Takashi; Okubo, Hiroshi

    2008-05-01

    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. PMID:18406435

  1. Phenolic metabolites of anthocyanins modulate mechanisms of endothelial function

    Edwards, Michael; Czank, Charles; Woodward, Gary; Cassidy, Aedin; Kay, Colin

    2015-01-01

    Anthocyanins are reported to have vascular bioactivity, however their mechanisms of action are largely unknown. Evidence suggests that anthocyanins modulate endothelial function, potentially by increasing nitric oxide (NO) synthesis, or enhancing NO bioavailability. This study compared the activity of cyanidin-3-glucoside, its degradation product protocatechuic acid, and phase II metabolite, vanillic acid. Production of NO and superoxide and expression of endothelial NO synthase (eNOS), NADPH...

  2. Anthocyanin Pigmentation Patternings in Petals of Hibiscus syriacus

    Kim, Jong Hwa; Okubo, Hiroshi; Fujieda, Kunimitsu; Uemoto, Shunpei

    1989-01-01

    Petals of Hibiscus syriacus are characterized by the various colored main part ‘body’ and an intense red to mauve ‘eye’ in the base of each petal. The concentrations of each anthocyanin varied greatly in the body part by the colors of the petals, while the predominant pigments were the cyanidin 3-glucoside and 3-malonylglucoside in the eye regions of all examined culivars. These pigmentation patternings were further investigated in several flowering stages; the anthocyanin pathways were disti...

  3. Anthocyanin synthesis in native and wound periderms of potato.

    Fogelman, Edna; Tanami, Sivan; Ginzberg, Idit

    2015-04-01

    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. PMID:25156080

  4. Anthocyanin Vacuolar Inclusions Form by a Microautophagy Mechanism.

    Chanoca, Alexandra; Kovinich, Nik; Burkel, Brian; Stecha, Samantha; Bohorquez-Restrepo, Andres; Ueda, Takashi; Eliceiri, Kevin W; Grotewold, Erich; Otegui, Marisa S

    2015-09-01

    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

  5. High acyl gellan as an emulsion stabilizer.

    Vilela, Joice Aline Pires; Cunha, Rosiane Lopes da

    2016-03-30

    High acyl gellan (0.01-0.2% w/w) was used as stabilizer in oil in water emulsions containing 30% (w/w) of sunflower oil and prepared under different process conditions. Stable emulsions to phase separation could be obtained using high acyl gellan (HA) content above 0.05% (w/w), while low acyl gellan (LA) prepared at the same conditions could not stabilize emulsions. Emulsions properties depended on the process used to mix the oil and gellan dispersion since high pressure homogenization favored stabilization while very high energy density applied by ultrasound led to systems destabilization. Emulsions prepared using high pressure homogenization showed zeta potential values ranging from -50 up to -59mV, suggesting that electrostatic repulsion could be contributing to the systems stability. Rheological properties of continuous phase were also responsible for emulsions stabilization, since HA gellan dispersions showed high viscosity and gel-like behavior. The high viscosity of the continuous phase could be associated to the presence of high acyl gellan microgels/aggregates. Disentanglement of these aggregates performed by ultrasound strongly decreased the viscosity and consequently affected the emulsions behavior, reducing the stability to phase separation. PMID:26794954

  6. Head-group acylation of monogalactosyldiacylglycerol is a common stress response, and the acyl-galactose acyl composition varies with the plant species and applied stress.

    Vu, Hieu Sy; Roth, Mary R; Tamura, Pamela; Samarakoon, Thilani; Shiva, Sunitha; Honey, Samuel; Lowe, Kaleb; Schmelz, Eric A; Williams, Todd D; Welti, Ruth

    2014-04-01

    Formation of galactose-acylated monogalactosyldiacylglycerols has been shown to be induced by leaf homogenization, mechanical wounding, avirulent bacterial infection and thawing after snap-freezing. Here, lipidomic analysis using mass spectrometry showed that galactose-acylated monogalactosyldiacylglycerols, formed in wheat (Triticum aestivum) and tomato (Solanum lycopersicum) leaves upon wounding, have acyl-galactose profiles that differ from those of wounded Arabidopsis thaliana, indicating that different plant species accumulate different acyl-galactose components in response to the same stress. Additionally, the composition of the acyl-galactose component of Arabidopsis acMGDG (galactose-acylated monogalactosyldiacylglycerol) depends on the stress treatment. After sub-lethal freezing treatment, acMGDG contained mainly non-oxidized fatty acids esterified to galactose, whereas mostly oxidized fatty acids accumulated on galactose after wounding or bacterial infection. Compositional data are consistent with acMGDG being formed in vivo by transacylation with fatty acids from digalactosyldiacylglycerols. Oxophytodienoic acid, an oxidized fatty acid, was more concentrated on the galactosyl ring of acylated monogalactosyldiacylglycerols than in galactolipids in general. Also, oxidized fatty acid-containing acylated monogalactosyldiacylglycerols increased cumulatively when wounded Arabidopsis leaves were wounded again. These findings suggest that, in Arabidopsis, the pool of galactose-acylated monogalactosyldiacylglycerols may serve to sequester oxidized fatty acids during stress responses. PMID:24286212

  7. Transcriptional regulation of anthocyanin biosynthesis in red cabbage.

    Yuan, Youxi; Chiu, Li-Wei; Li, Li

    2009-11-01

    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 green varieties had negligible amount of anthocyanins under normal growth condition, the four red cultivars contained up to 1.60 mg g(-1) fresh weight. HPLC analysis of the four red cultivars revealed that they produced similar composition of various forms of cyanidin glucosides but at different concentrations. Molecular analysis indicated that all the red cabbage shared common mechanism of regulatory control for anthocyanin biosynthesis. Except CHI which showed similar expression levels between green and red cultivars, the other structural genes, CHS, F3H, F3'H, DFR, LDOX, and GST, were constitutively up-regulated during all stages of vegetative growth in red varieties. The expression of these structural genes was also dramatically increased in green and red cabbage under nutrient stresses. The increased expression of the structural genes coincided with a coordinated increase in transcript levels of a bHLH gene, BoTT8, and a MYB transcription factor, BoMYB2. These results indicate that activation of these two regulatory factors by unknown mechanisms constitutively up-regulates nearly the entire pathway genes for the onset of anthocyanin biosynthesis in red cabbage. Moreover, the amount of total anthocyanins in red cabbage was found to be positively correlated with total antioxidant power, implicating the potential health benefit of red cabbage to human health. PMID:19756724

  8. Anthocyanins are bioavailable in humans following an acute dose of cranberry juice

    Research suggests that anthocyanins from berry fruit may affect a variety of physiological responses, including endothelial function, but little information is available regarding the pharmacokinetics of these flavonoids in humans. To determine the pharmacokinetics of cranberry anthocyanins a study ...

  9. Mesophyll-localized phytochromes gate stress- and light-inducible anthocyanin accumulation in Arabidopsis thaliana

    Oh, Sookyung; Warnasooriya, Sankalpi N.; Montgomery, Beronda L.

    2014-01-01

    Abiotic stress and light induce anthocyanin accumulation in Arabidopsis. Here, we demonstrate that mesophyll-localized phytochromes regulate nitrogen-, phosphate- and cold-induced anthocyanin accumulation in shoots of Arabidopsis. Whereas ecotype-dependent differences result in distinct total levels of anthocyanin accumulation in response to light, cold, or nutrient-deficient treatments, phytochromes generally gate light- and/or stress-induced anthocyanin accumulation in shoots, as plants dep...

  10. Phenolic metabolites of anthocyanins following a dietary intervention study in post-menopausal women

    de Ferrars, Rachel M; Cassidy, Aedín; Curtis, Peter; Kay, Colin D.

    2014-01-01

    Scope Numerous studies feeding anthocyanin-rich foods report limited bioavailability of the parent anthocyanins. The present study explores the identity and concentration of the phenolic metabolites of anthocyanins in humans. Methods and results Anthocyanin metabolites were quantified in samples collected from a previously conducted 12-wk elderberry intervention study in healthy post-menopausal women. Individual 1-, 2- and 3-h post-bolus urine samples and pooled plasma samples following acute...

  11. Low Medium pH Value Enhances Anthocyanin Accumulation in Malus Crabapple Leaves

    Yanchen Zhang; Jie Zhang; Tingting Song; Jinyan Li; Ji Tian; Kaina Jin; Yuncong Yao

    2014-01-01

    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 cy...

  12. Tissue- and isoform-specific phytochrome regulation of light-dependent anthocyanin accumulation in Arabidopsis thaliana

    Warnasooriya, Sankalpi N.; Porter, Katie J.; Montgomery, Beronda L

    2011-01-01

    Phytochromes regulate light- and sucrose-dependent anthocyanin synthesis and accumulation in many plants. Mesophyll-specific phyA alone has been linked to the regulation of anthocyanin accumulation in response to far-red light in Arabidopsis thaliana. However, multiple mesophyll-localized phytochromes were implicated in the photoregulation of anthocyanin accumulation in red-light conditions. Here, we report a role for mesophyll-specific phyA in blue-light-dependent regulation of anthocyanin l...

  13. Early Autumn Senescence in Red Maple (Acer rubrum L.) Is Associated with High Leaf Anthocyanin Content

    Rachel Anderson; Peter Ryser

    2015-01-01

    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 consiste...

  14. Purification and characterization of fatty acyl-acyl carrier protein synthetase from Vibrio harveyi.

    Fice, D; Shen, Z; Byers, D M

    1993-01-01

    A Vibrio harveyi enzyme which catalyzes the ATP-dependent ligation of fatty acids to acyl carrier protein (ACP) has been purified 6,000-fold to apparent homogeneity by anion-exchange, gel filtration, and ACP-Sepharose affinity chromatography. Purified acyl-ACP synthetase migrated as a single 62-kDa band on sodium dodecyl sulfate-polyacrylamide gel electrophoresis and as an 80-kDa protein by gel filtration under reducing conditions. Activity of the purified enzyme was lost within hours in the absence of glycerol and low concentrations of Triton X-100. Acyl-ACP synthetase exhibited Kms for myristic acid, ACP, and ATP of 7 microM, 18 microM, and 0.3 mM, respectively. The enzyme was specific for adenine-containing nucleotides, and AMP was the product of the reaction. No covalent acyl-enzyme intermediate was observed. Enzyme activity was stimulated up to 50% by iodoacetamide but inhibited > 80% by N-ethylmaleimide: inhibition by the latter was prevented by ATP and ACP but not myristic acid. Dithiothreitol and sulfhydryl-directed reagents also influenced enzyme size, activity, and elution pattern on anion-exchange resins. The function of acyl-ACP synthetase has not been established, but it may be related to the capacity of V. harveyi to elongate exogenous fatty acids by an ACP-dependent mechanism. Images PMID:8384617

  15. Acylation of Toluene with Isobutyryl Chloride

    Čejka, Jiří; Klisáková, Jana; Žilková, Naděžda; Červený, L.

    Cape Town, 2004 - ( Steen van, E.), s. 2717-2723 ISBN 0-958-46636-X. [International Zeolite Conference /14./. Cape Town (ZA), 25.04.2004-30.04.2004] R&D Projects: GA ČR GA203/03/0804 Institutional research plan: CEZ:AV0Z4040901 Keywords : acylation of toluene * isobutyryl chloride * zeolites Subject RIV: CF - Physical ; Theoretical Chemistry

  16. Applying Acylated Fucose Analogues to Metabolic Glycoengineering

    Julia Rosenlöcher; Verena Böhrsch; Michael Sacharjat; Véronique Blanchard; Christoph Giese; Volker Sandig; Christian P R Hackenberger; Stephan Hinderlich

    2015-01-01

    Manipulations of cell surface glycosylation or glycan decoration of selected proteins hold immense potential for exploring structure-activity relations or increasing glycoprotein quality. Metabolic glycoengineering describes the strategy where exogenously supplied sugar analogues intercept biosynthetic pathways and are incorporated into glycoconjugates. Low membrane permeability, which so far limited the large-scale adaption of this technology, can be addressed by the introduction of acylated...

  17. Isolation and Characterization of Anthocyanins from Hibiscus sabdariffa Flowers.

    Grajeda-Iglesias, Claudia; Figueroa-Espinoza, Maria C; Barouh, Nathalie; Baréa, Bruno; Fernandes, Ana; de Freitas, Victor; Salas, Erika

    2016-07-22

    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. PMID:27312226

  18. Thermal degradation of anthocyanins from purple potato (Cv. Purple Majesty) and their impact on antioxidant capacity

    Degradation parameters of purified anthocyanins from purple-fleshed potato (Purple Majesty cv.) heated at high temperatures (100 - 150 °C) was determined. Purified anthocyanins, prepared by removing salts, sugars and colorless non-anthocyanin phenolics from the crude extract, were quantified using H...

  19. Isolation and Purification of Anthocyanins from Black Bean Wastewater Using Macroporous Resins

    Wang, Xiaoxi

    2012-01-01

    Isolation and purification of anthocyanins from black bean canning wastewater by column chromatography with macroporous resins were investigated in this study. Different adsorption materials and adsorption conditions were compared and the most effective material and adsorption conditions were selected to purify anthocyanins. Purified anthocyanins then were identified by high performance liquid chromatography electrospray tandem mass spectrometry. The most effective macroporous resin was selec...

  20. Purification and characterization of fatty acyl-acyl carrier protein synthetase from Vibrio harveyi.

    Fice, D; Z. Shen; Byers, D M

    1993-01-01

    A Vibrio harveyi enzyme which catalyzes the ATP-dependent ligation of fatty acids to acyl carrier protein (ACP) has been purified 6,000-fold to apparent homogeneity by anion-exchange, gel filtration, and ACP-Sepharose affinity chromatography. Purified acyl-ACP synthetase migrated as a single 62-kDa band on sodium dodecyl sulfate-polyacrylamide gel electrophoresis and as an 80-kDa protein by gel filtration under reducing conditions. Activity of the purified enzyme was lost within hours in the ...

  1. N-acylation of ethanolamine using lipase: a chemoselective catalyst

    Mazaahir Kidwai; Roona Poddar; Poonam Mothsra

    2009-01-01

    The N-acylation of ethanolamine (2) with various fatty acids 1a–d and esters of fatty acids 1e–h using Candida antarctica B lipase (Novozym® 435) are described and optimum conditions for selective N-acylation rather than O-acylation are also discussed. Microwave assisted solution phase, solid supported and conventional methods were investigated and results were compared. There is a synergy between the enzyme catalysis and microwave irradiation.

  2. N-acylation of ethanolamine using lipase: a chemoselective catalyst

    Mazaahir Kidwai

    2009-03-01

    Full Text Available The N-acylation of ethanolamine (2 with various fatty acids 1a–d and esters of fatty acids 1e–h using Candida antarctica B lipase (Novozym® 435 are described and optimum conditions for selective N-acylation rather than O-acylation are also discussed. Microwave assisted solution phase, solid supported and conventional methods were investigated and results were compared. There is a synergy between the enzyme catalysis and microwave irradiation.

  3. Analytical procedures for identifying anthocyanins in natural extracts

    Anthocyanins are among the most important plant pigments. Due to their potential benefits for human health, there is considerable interest in these natural pigments. Nonetheless, there is great difficulty in finding a technique that could provide the identification of structurally similar compounds and estimate the number and concentration of the species present. A lot of techniques have been tried to find the best methodology to extract information from these systems. In this paper, a review of the most important procedures is given, from the extraction to the identification of anthocyanins in natural extracts. (author)

  4. Evaluation of red cabbage anthocyanins after partial purification on clay

    Toni Jefferson Lopes

    2011-12-01

    Full Text Available The aim of this work was to evaluate the red cabbage anthocyanins quality after purification by static adsorption assays on clay (Tonsil Terrana 580FF. Thin-layer chromatography analysis and scan spectrometry on UV-Visible showed a good dye stability of the pigment interacting with the clay. The use of pH 3.0 buffer during the batch assays provided a protective effect on the cabbage anthocyanins, limiting the dye acid hydrolyses. Analyses of the reducing sugars contents of the extract showed that clay retained 20% average of total free sugars under the test conditions.

  5. Plasma levels of acylated ghrelin in patients with functional dyspepsia

    Yeon Soo Kim; Joon Seong Lee; Tae Hee Lee; Joo Young Cho; Jin Oh Kim; Wan Jung Kim; Hyun Gun Kim; Seong Ran Jeon; Hoe Su Jeong

    2012-01-01

    AIM:To investigate the relationship between plasma acylated ghrelin levels and the pathophysiology of functional dyspepsia.METHODS:Twenty-two female patients with functional dyspepsia and twelve healthy volunteers were recruited for the study.The functional dyspepsia patients were each diagnosed based on the Rome Ⅲ criteria.Eligible patients completed a questionnaire concerning the severity of 10 symptoms.Plasma acylated ghrelin levels before and after a meal were determined in the study participants using a commercial human acylated enzyme immunoassay kit; electrogastrograms were performed for 50 min before and after a standardized 10-min meal containing 265 kcal.RESULTS:There were no significant differences in plasma acylated ghrelin levels between healthy volunteers and patients with functional dyspepsia.However,in patients with functional dyspepsia,there was a negative correlation between fasting plasma acylated ghrelin levels and the sum score of epigastric pain (r =-0.427,P =0.047) and a positive correlation between the postprandial/fasting plasma acylated ghrelin ratio and the sum score of early satiety (r =0.428,P =0.047).Additionally,there was a negative correlation between fasting acylated ghrelin plasma levels and fasting normogastria (%) (r =-0.522,P =0.013).Interestingly,two functional dyspepsia patients showed paradoxically elevated plasma acylated ghrelin levels after the meal.CONCLUSION:Abnormal plasma acylated ghrelin levels before or after a meal may be related to several of the dyspeptic symptoms seen in patients with functional dyspepsia.

  6. Effect of Sugar Treatment on Stability of Anthocyanin Pigments in Berries

    E. Nikkhah

    2007-01-01

    Full Text Available Anthocyanins are natural pigments widely distributed in nature. Anthocyanin color molecules are a subclass of flavonoids. They are responsible for the reds, purples and blues in many flowers, fruits and vegetables. Fruits and berries are the most sample sources of anthocyanins in nature. Berries and fruits are an important part of the Finnish diet. In many researches the positive effect of fruit and berry intake on human health has been reported. Anthocyanins are considered to contribute to the healthiness of fruits and berries for their antioxidant, anti-carcinogenic, anti-inflammatory and anti-angiogenic properties for example. Anthocyanins can also improve the nutritional value of processed foods by preventing oxidation of lipids and proteins in the food products. However, the stability of anthocyanins becomes most significant also in this case, as in the case of color quality. In this study the anthocyanin pigment was extracted from the three different berries (Morus nigra L., Morus alba var. nigra and Fragaria L.. Using the soaking and wetting in ethanol (1% acidified. The extracted anthocyanin pigments then were exposed to three different concentration of sugar (sucrose (20, 40 and 60%. Three groups of anthocyanin solutions keeping in darkness and refrigerator for 63 days and per 3 week, the quantity of anthocyanin absorbance recorded in 520 nm. In this study, according to statistical analysis, primary concentration (20% of sugar (sucrose has protective effect on Anthocyanins, but in higher concentration this effect is decreased.

  7. Conventional, ultrasound-assisted, and accelerated-solvent extractions of anthocyanins from purple sweet potatoes.

    Cai, Zhan; Qu, Ziqian; Lan, Yu; Zhao, Shujuan; Ma, Xiaohua; Wan, Qiang; Jing, Pu; Li, Pingfan

    2016-04-15

    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). PMID:26616949

  8. Identification of anthocyanins in the liver, eye, and brain of blueberry-fed pigs.

    Kalt, Wilhelmina; Blumberg, Jeffrey B; McDonald, Jane E; Vinqvist-Tymchuk, Melinda R; Fillmore, Sherry A E; Graf, Brigitte A; O'Leary, Jennifer M; Milbury, Paul E

    2008-02-13

    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 used to examine the deposition of anthocyanins in tissues including the liver, eye, and brain tissue. Pigs were fed diets supplemented with 0, 1, 2, or 4% w/w blueberries ( Vaccinium corymbosum L. 'Jersey') for 4 weeks. Prior to euthanasia, pigs were fasted for 18-21 h. Although no anthocyanins were detected in the plasma or urine of the fasted animals, intact anthocyanins were detected in all tissues where they were sought. LC-MS/MS results are presented for the relative concentration of 11 intact anthocyanins in the liver, eye, cortex, and cerebellum. The results suggest that anthocyanins can accumulate in tissues, including tissues beyond the blood-brain barrier. PMID:18211026

  9. Acyl-acyl carrier protein as a source of fatty acids for bacterial bioluminescence

    Pulse-chase experiments with [3H]tetradecanoic acid and ATP showed that the bioluminescence-related 32-kDa acyltransferase from Vibrio harveyi can specifically catalyze the deacylation of a 3H-labeled 18-kDa protein observed in extracts of this bacterium. The 18-kDa protein has been partially purified and its physical and chemical properties strongly indicate that it is fatty acyl-acyl carrier protein (acyl-ACP). Both this V. harveyi [3H]acylprotein and [3H]palmitoyl-ACP from Escherichia coli were substrates in vitro for either the V. harveyi 32-kDa acyltransferase or the analogous enzyme (34K) from Photobacterium phosphoreum. TLC analysis indicated that the hexane-soluble product of the reaction is fatty acid. No significant cleavage of either E. coli or V. harveyi tetradecanoyl-ACP was observed in extracts of these bacteria unless the 32-kDa or 34K acyltransferase was present. Since these enzymes are believed to be responsible for the supply of fatty acids for reduction to form the aldehyde substrate of luciferase, the above results suggest that long-chain acyl-ACP is the source of fatty acids for bioluminescence

  10. Veronica: Acylated flavone glycosides as chemosystematic markers

    Albach, Dirk C.; Grayer, Renée J.; Kite, Geoffrey C.;

    2005-01-01

    HPLC/DAD and LCeMS of an extract of Veronica spicata subgenus Pseudolysimachium, Plantaginaceae) revealed the presence of six 6-hydroxyluteolin glycosides acylated with phenolic acids, three of which are new compounds and which we called spicosides. A flavonoid survey of seven more species...... instead. Spicosides appeared to be common in subgenus Pseudolysimachium (detected in five out of eight species), but we did not find them in subgenus Pentasepalae. Previously, acetylated 8-hydroxyflavone glycosides have been isolated from or detected in eight species of V. subgenus Pentasepalae (in 13...

  11. Acyl Structure Regulates Galactosylceramide's Interfacial Interactions†

    Ali, Shaukat; Smaby, Janice M.; Brown, Rhoderick E.

    1993-01-01

    Galactosylceramides (GalCer) with homogeneous acyl chains containing zero, one, or two cis double bonds have been synthesized and characterized at an argon-aqueous buffer interface using a Langmuir film balance. Both surface pressure and surface potential were measured as a function of molecular area at 24 °C. N-Lignoceroylgalactosylsphingosine (N-24:0-GalSph), N-stearoylgalactosylsphingosine (N-18:0-GalSph), and N-palmitoylgalactosylsphingosine (N-16:0-GalSph) form condensed films that are s...

  12. Sugar Maple Phenology: Anthocyanin Production During Leaf Senescence

    Lindgren, E.; Rock, B.

    2007-12-01

    The Northeastern United States is known for its brilliant fall foliage colors. Foliage is responsible for a billion dollar tourism industry. Many comment that past years have not resulted in the amazing color displays seen historically. As sugar maple trees senesce they contribute bright red leaves to the mural of oranges, yellows, and greens. The pigment that produces the red color, anthocyanin, is synthesized in the fall as chlorophyll slowly degrades. Remote sensing data from LandSat during fall senescence can help investigate this event by quantifying color change and intensity. This data can then be compared to ground validation efforts in several study plots. The results will help answer the question, "Why do leaves turn red?" One hypothesis is that this pigment acts as a photoprotectant and screens leaves from UV light. It is possible that an increase in tropospheric ozone has negatively affected fall foliage due to the increased reflection of UV light before it reaches the trees; thereby reducing the leaves need to produce anthocyanin. Another hypothesis is that production of anthocyanin is linked to temperature, with maximum synthesis occurring during cold evenings and moderate days. Temperature changes caused by climate change could also be affecting anthocyanin. Through observing these changes by remote sensing and ground experiments, more can be learned about this phenological stage and why it happens.

  13. Putative neuroprotective actions of N-acyl-ethanolamines

    Hansen, Harald S.; Moesgaard, B.; Petersen, G.;

    2002-01-01

    N-Acyl-ethanolamines (NAEs) and their precursors, N-acyl-ethanolamine phospholipids (NAPEs), are present in the mammalian brain at levels of a few hundred picomoles/gram tissue and a few nanomoles/gram tissue, respectively. NAE-containing arachidonic acid is called anandamide, and it has attracted...

  14. Understanding Acyl Chain and Glycerolipid Metabolism in Plants

    Ohlrogge, John B.

    2013-11-05

    Progress is reported in these areas: acyl-editing in initial eukaryotic lipid assembly in soybean seeds; identification and characterization of two Arabidopsis thaliana lysophosphatidyl acyltransferases with preference for lysophosphatidylethanolamine; and characterization and subcellular distribution of lysolipid acyl transferase activity of pea leaves.

  15. Oxidative activation of dihydropyridine amides to reactive acyl donors

    Funder, Erik Daa; Trads, Julie Brender; Gothelf, Kurt Vesterager

    2015-01-01

    Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium...

  16. Foliar anthocyanin content - Sensitivity of vegetation indices using green reflectance

    Vina, A.; Gitelson, A. A.

    2009-12-01

    The amount and composition of photosynthetic and non-photosynthetic foliar pigments varies primarily as a function of species, developmental and phenological stages, and environmental stresses. Information on the absolute and relative amounts of these pigments thus provides insights onto the physiological conditions of plants and their responses to stress, and has the potential to be used for evaluating plant species composition and diversity across broad geographic regions. Anthocyanins in particular, are non-photosynthetic pigments associated with the resistance of plants to environmental stresses (e.g., drought, low soil nutrients, high radiation, herbivores, and pathogens). As they absorb radiation primarily in the green region of the electromagnetic spectrum (around 540-560 nm), broad-band vegetation indices that use this region in their formulation will respond to their presence. We evaluated the sensitivity of three vegetation indices using reflectance in the green spectral region (the green Normalized Difference Vegetation Index, gNDVI, the green Chlorophyll Index, CIg, and the Visible Atmospherically Resistant Vegetation Index, VARI) to foliar anthocyanins in five different species. For comparison purposes the widely used Normalized Difference Vegetation Index, NDVI was also evaluated. Among the four indices tested, the VARI, which uses only spectral bands in the visible region of the electromagnetic spectrum, was found to be inversely and linearly related to the relative amount of foliar anthocyanins. While this result was obtained at leaf level, it opens new possibilities for analyzing anthocyanin content across multiple scales, by means of currently operational aircraft- and spacecraft-mounted broad-band sensor systems. Further studies that evaluate the sensitivity of the VARI to the relative content of anthocyanins across space (e.g., at canopy and regional scales) and time, and its relationship with plant biodiversity and vegetation stresses, are

  17. Erbium trifluoromethanesulfonate-catalyzed Friedel–Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation

    Tran, Phuong Hoang; Hansen, Poul Erik; Nguyen, Hai Truong;

    2015-01-01

    Erbium trifluoromethanesulfonate is found to be a good catalyst for the Friedel–Crafts acylation of arenes containing electron-donating substituents using aromatic carboxylic acids as the acylating agents under microwave irradiation. An effective, rapid and waste-free method allows the preparation...... of a wide range of aryl ketones in good yields and in short reaction times with minimum amounts of waste...

  18. Acyl-CoA-binding protein (ACBP) can mediate intermembrane acyl-CoA transport and donate acyl-CoA for beta-oxidation and glycerolipid synthesis

    Rasmussen, J T; Færgeman, Nils J.; Kristiansen, K;

    1994-01-01

    , were much lower than expected. ACBP was able to extract hexadecanoyl-CoA from phosphatidylcholine membranes immobilized on a nitrocellulose membrane. The acyl-CoA/ACBP complex formed was able to transport acyl-CoA to mitochondria or microsomes in suspension, or to microsomes immobilized on a...... nitrocellulose membrane, and to donate them to beta-oxidation or glycerolipid synthesis in mitochondria or microsomes, respectively....

  19. Friedel-Craft Acylation of ar-Himachalene: Synthesis of Acyl-ar-Himachalene and a New Acyl-Hydroperoxide

    Abdallah Karim

    2011-07-01

    Full Text Available Friedel-Craft acylation at 100 °C of 2,5,9,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene [ar-himachalene (1], a sesquiterpenic hydrocarbon obtained by catalytic dehydrogenation of α-, β- and γ-himachalenes, produces a mixture of two compounds: (3,5,5,9-tetramethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl-ethanone (2, in 69% yield, with a conserved reactant backbone, and 3, with a different skeleton, in 21% yield. The crystal structure of 3 reveals it to be 1-(8-ethyl-8-hydroperoxy-3,5,5-trimethyl-5,6,7,8-tetrahydronaphthalen-2-yl-ethanone. In this compound O-H…O bonds form dimers. These hydrogen-bonds, in conjunction with weaker C-H…O interactions, form a more extended supramolecular arrangement in the crystal.

  20. Palladium-Catalyzed Environmentally Benign Acylation.

    Suchand, Basuli; Satyanarayana, Gedu

    2016-08-01

    Recent trends in research have gained an orientation toward developing efficient strategies using innocuous reagents. The earlier reported transition-metal-catalyzed carbonylations involved either toxic carbon monoxide (CO) gas as carbonylating agent or functional-group-assisted ortho sp(2) C-H activation (i.e., ortho acylation) or carbonylation by activation of the carbonyl group (i.e., via the formation of enamines). Contradicting these methods, here we describe an environmentally benign process, [Pd]-catalyzed direct carbonylation starting from simple and commercially available iodo arenes and aldehydes, for the synthesis of a wide variety of ketones. Moreover, this method comprises direct coupling of iodoarenes with aldehydes without activation of the carbonyl and also without directing group assistance. Significantly, the strategy was successfully applied to the synthesis n-butylphthalide and pitofenone. PMID:27377566

  1. Anthocyanins: Model Compounds for Learning about More than pH

    Curtright, Robert; Rynearson, James A.; Markwell, John

    1996-04-01

    We have all experienced anthocyanins as a part of the natural beauty of the plant world. Anthocyanins provide a startling contrast to an otherwise green world producing the beauty of garden-variety flowers, wildflowers, and the blazing colors of many trees, bushes, and berries. We believe that anthocyanins deserve a more prominent role as models for engaging student interest in basic chemical principles. In recent years it has become common to use anthocyanins as pH indicators. We believe that chemistry teachers can capitalize further on the natural interest of students in anthocyanin pigments to design meaningful lessons involving chromatography and hydrolysis. This article focuses on the use of anthocyanins in chromatography and hydrolysis.

  2. The protective effect of blueberry anthocyanins against perfluorooctanoic acid-induced disturbance in planarian (Dugesia japonica).

    Yuan, Zuoqing; Zhang, Jianyong; Tu, Changchao; Wang, Zhijing; Xin, Wenpeng

    2016-05-01

    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. PMID:26836138

  3. Anthocyanin copigmentation and color of wine: The effect of naturally obtained hydroxycinnamic acids as cofactors.

    Bimpilas, Andreas; Panagopoulou, Marilena; Tsimogiannis, Dimitrios; Oreopoulou, Vassiliki

    2016-04-15

    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. PMID:26616922

  4. Purification and characterization of glycosyltransferases involved in anthocyanin biosynthesis in cell-suspension cultures of Daucus carota L

    The major anthocyanins accumulated by an Afghan cultivar of Daucus carota L. are cyanidin 3-(xylosylglucosylgalactosides) acylated with sinapic or ferulic acid. The formation of the branched triglycoside present as a common structural element requires an ordered sequence of glycosylation events. Two of these enzymic glycosylation reactions have been detected in protein preparations from carrot cell-suspension cultures. The first step is a galactosyl transfer catalyzed by UDP-galactose: cyanidin galactosyltransferase (CGT) resulting in cyanidin 3-galactoside. The putative second step is the formation of cyanidin 3-(xylosylgalactoside) catalyzed by UDP-xylose: cyanidin 3-galactoside xylosyltransferase (CGXT). Both enzyme activities were characterized from crude protein preparations. The CGT was purified 526-fold from the cytosolic fraction of UV-irradiated cell cultures by ion-exchange chromatography on diethylaminoethyl (DEAE)-Sephacel, affinity chromatography on Blue Sepharose CL-6B, gel permeation chromatography on Sephadex G-75 and elution from the gel matrix after non-dissociating PAGE. Its molecular mass was estimated by SDS-PAGE and by calibrated gel permeation chromatography on Sephadex G-75. In both cases a molecular mass of 52 kDa was determined, indicating that the native protein is a monomer of 52 kDa. The galactosyl transfer and the xylosyl transfer are presumed to be catalyzed by separate enzymes. (author)

  5. Thermodynamics of ligand binding to acyl-coenzyme A binding protein studied by titration calorimetry

    Færgeman, Nils J.; Sigurskjold, B W; Kragelund, B B;

    1996-01-01

    Ligand binding to recombinant bovine acyl-CoA binding protein (ACBP) was examined using isothermal microcalorimetry. Microcalorimetric measurements confirm that the binding affinity of acyl-CoA esters for ACBP is strongly dependent on the length of the acyl chain with a clear preference for acyl-...

  6. Optimization of Ultrasound-Assisted Extraction of Anthocyanins from Mulberry, Using Response Surface Methodology

    Ren-You Gan; Wen-Hua Ling; Tang-Bin Zou; Min Wang

    2011-01-01

    Mulberry is one of the most widely used traditional Chinese medicines. Anthocyanins are the main bioactive components of mulberry, and possess important biological activities, such as antimicrobial, anti-inflammatory and antioxidant activities. This study investigated the ultrasound-assisted extraction (UAE) of anthocyanins from mulberry by using response surface methodology (RSM). The extraction conditions associated with anthocyanin yield, including extraction solvent, liquid-to-solid rate,...

  7. Effect of Light on Anthocyanin Levels in Submerged, Harvested Cranberry Fruit

    Yu Zhou; Bal Ram Singh

    2004-01-01

    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 tha...

  8. Effect of calcium on strawberry fruit flavonoid pathway gene expression and anthocyanin accumulation.

    Xu, Wenping; Peng, Hui; Yang, Tianbao; Whitaker, Bruce; Huang, Luhong; Sun, Jianghao; Chen, Pei

    2014-09-01

    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. PMID:25036468

  9. Prevention of thermal degradation of red currant juice anthocyanins by phenolic compounds addition

    Kopjar, Mirela; Piližota, Vlasta; Šubarić, D.; Babić, J.

    2009-01-01

    The aim of this study was investigation of prevention of thermal degradation of the red currant juice anthocyanins by addition of different phenolic compounds (catechol, 4-methyl catechol, catechin, chlorogenic acid and gallic acid). Phenolic compounds were added in 50:1 and 100:1 copigment:pigment molar ratio. Red currant juice samples were heated at 30, 50, 70 and 90 °C for 1 hour. Thermal degradation of anthocyanins was investigated through determination of anthocyanin content and calculat...

  10. Characterisation of Vranec, Cabernet sauvignon and Merlot wines based on their chromatic and anthocyanin profiles

    Dimitrovska Maja; Tomovska Elena; Bocevska Mirjana

    2013-01-01

    Wines of three different grape varieties, Vranec, Cabernet Sauvignon and Merlot were examined for their characterisation in terms of anthocyanin and chromatic profiles, total polyphenols and antioxidant potential. Total, monomeric, polymeric and copigmented anthocyanins were determined by spectrophotometry and the individual anthocyanin compounds were quantified using HPLC-DAD. Chromatic profile was evaluated according to colour density, hue, % red, % blue, % yellow and brilliance (% dA...

  11. Impact of Frozen Storage on the Anthocyanin and Polyphenol Content of American Elderberry Fruit Juice

    Johnson, Mitch C.; Thomas, Andrew L.; Greenlief, C. Michael

    2015-01-01

    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 ...

  12. Methylation Formation to Improve Red Radish Anthocyanins Solubility in Cold Water

    Jie Zhang; Xiaohua Zhou; Dan Wang; Xing Zhou; Shiyu Tan

    2013-01-01

    This paper introduced an approach by methylation formation to enhance the solubility of red radish anthocyanins in cold water. FTIR spectrums indicated the formation of methylated red radish anthocyanins. The methylation yeild was 81.4 % under optimized conditions. The solubility of methylated red radish anthocyanins could reach 10.7 mg/mL in cold water (4 °C). They were water soluble, which facilitated them incorporation into aqueous food systems. And the evolution of CIELab has been studied...

  13. ACIDIC SOAKING AND STEAM BLANCHING RETAIN ANTHOCYANINS AND POLYPHENOLS IN PURPLE Dioscorea alata FLOUR

    Nelis Imanningsih; Deddy Muchtadi 2); Tutik Wresdiyati2); Nurheni Sri Palupi; Komari

    2013-01-01

    Purple Dioscorea alata (DA) tuber has health benefits due to its bioactive anthocyanins, which belong to polyphenolic group. Tuber is commonly made into flour to optimize its uses, however, the anthocyanins undergo significant degradation during processing because of the endogenous polyphenol oxidase activities. This research investigated factors that retain anthocyanins and polyphenols in the purple DA flour as well as its antioxidant capacity. The types of treatments during milling process ...

  14. Anthocyanin-dependent anoxygenic photosynthesis in coloured flower petals?

    Lysenko, Vladimir; Varduny, Tatyana

    2013-11-01

    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.

  15. Anthocyanin extracts with antioxidant and radical scavenging effect

    Gabrielska, J.; Langner, M. [Technical Univ. Wroclaw (Poland). Dept. of Physics and Biophysics; Oszmianski, J. [Technical Univ. Wroclaw (Poland). Dept. of Fruit and Vegetable Technology; Komorowska, M. [Politechnika Wroclawska, Wroclaw (Poland). Inst. Fizyki

    1999-06-01

    The antioxidative activity of three anthocyanin pigments, extracted from the fruits of chokeberry, honeysuckle and sloe, were studied. Lipid oxidation in the liposome membrane, induced by UV radiation, was evaluated with a thiobarbituric acid-reactive substances assay. The antioxidant efficiency of the studied compounds follows this sequence: chokeberry>sloe>honeysuckle. The extract concentrations at which a 50% reduction of phosphatidylcholine oxidation was observed, were respectively: 48, 54 and 60 mg/l. The end products of lipid membrane oxidation were evaluated using HPLC. It was found that the antioxidative potency of anthocyanin extracts is concentration-dependent. As shown by EPR technique the efficiency of the extracts to eliminate free radicals from the solution follows the order of the antioxidant activity. (orig.)

  16. Anthocyanin extracts with antioxidant and radical scavenging effect

    The antioxidative activity of three anthocyanin pigments, extracted from the fruits of chokeberry, honeysuckle and sloe, were studied. Lipid oxidation in the liposome membrane, induced by UV radiation, was evaluated with a thiobarbituric acid-reactive substances assay. The antioxidant efficiency of the studied compounds follows this sequence: chokeberry>sloe>honeysuckle. The extract concentrations at which a 50% reduction of phosphatidylcholine oxidation was observed, were respectively: 48, 54 and 60 mg/l. The end products of lipid membrane oxidation were evaluated using HPLC. It was found that the antioxidative potency of anthocyanin extracts is concentration-dependent. As shown by EPR technique the efficiency of the extracts to eliminate free radicals from the solution follows the order of the antioxidant activity. (orig.)

  17. Does the accumulation of anthocyanins protect the plant against photoinhibition?

    Bargaila, Kestutis; Zhang, Lulu; Cekaliovaite, Marija; Hansen, Paula Melo Paulon; Sloth, Stine Hesselholt; Zhang, Xiaoting

    2008-01-01

    The aim of this second semester project is to find out whether the pigment anthocyanin (a pigment responsible for the vermilion in plants) offers plants, any protection against Photoinhibition. The plant called Gaultheria miqueliana has been chosen to be the object of study of this project because it has characteristics, which are important for the beginning of the project - green and red leaves. The plants were exposed to different light intensities and afterwards the electron transport rate...

  18. Transcriptional control of floral anthocyanin pigmentation in monkeyflowers (Mimulus)

    Yuan, Yao-Wu; Sagawa, Janelle M.; Frost, Laura; Vela, James P.; Bradshaw, Harvey D.

    2014-01-01

    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 th...

  19. Antioxidation of Anthocyanins in Photosynthesis Under High Temperature Stress

    Ling Shao; Zhan Shu; Shu-Lan Sun; Chang-Lian Peng; Xiao-Jing Wang; Zhi-Fang Lin

    2007-01-01

    Chlorophyll fluorescence and antioxidative capability in detached leaves of the wild type Arabidopsis thaliana L. ecotype Landsberg erecta (Ler) and three mutants deficient in anthocyanins biosynthesis (tt3, tt4, and tt3tt4) were investigated during treatment with temperatures ranging 25-45 ℃. In comparison with the wild type, chlorophyll fluorescence parameters Fv/Fm, ΦPSⅡ, electron transport rate (ETR), Fv/Fo and qP in three anthocyanin-deficient mutants showed a more rapidly decreasing rate when the temperature was over 35 ℃. Non-photochemical quenching (NPQ) in these mutants was almost completely lost at 44 ℃, whereas the content of heat stable protein dropped and the rate of the membrane leakage increased.Fo-temperature curves were obtained by monitoring Fo levels with gradually elevated temperatures from 22 ℃ to 72 ℃ at 0.5℃/min. The inflexion temperatures of Fo were 45.8 ℃ in Ler, 45.1 ℃ in tt3, 44.1 ℃ in tt4 and 42.3 ℃ in tt3tt4, respectively.The temperatures of maximal Fo in three mutants were 1.9-3.8 ℃ lower than the wild type plants. Meanwhile, three mutants had lower activities of superoxide dismutase (SOD) and ascorbate peroxidase (APX) and an inferior scavenging capability to DPPH (1.1-diphenyl-2-picrylhy.drazyl) radical under heat stress, and in particular tt3tt4 had the lowest antioxidative potential. The results of the diaminobenzidine-H2O2 histochemical staining showed that H2O2 was accumulated in the leaf vein and mesophyll cells of mutants under treatment at 40 ℃, and it was significantly presented in leaf cells of tt3tt4.The sensitivity of Arabidopsis anthocyanins-deficient mutants to high temperatures has revealed that anthocyanins in normal plants might provide protection from high temperature injury, by enhancing its antioxidative capability under high temperature stress.

  20. Anthocyanin-dependent anoxygenic photosynthesis in coloured flower petals?

    Vladimir Lysenko; Tatyana Varduny

    2013-01-01

    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 ...

  1. Early Autumn Senescence in Red Maple (Acer rubrum L. Is Associated with High Leaf Anthocyanin Content

    Rachel Anderson

    2015-08-01

    Full Text Available 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.

  2. Fluorescence of anthocyanin pigments in plant extracts at various pH

    Pliszka, Barbara; Olszewska, Teresa; Drabent, Regina

    2001-07-01

    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.

  3. Coronatine Induces an Accumulation of Anthocyanin and Starch in Purple-fleshed Sweetpotato (Ipomoea batatas Lam.)

    Baoqing WANG; Beitao XIE; Haiyan ZHANG; Liming ZHANG; Qingmei WANG

    2013-01-01

    [Objective] The objective of this research was to examine the effects of COR on anthocyanin and starch content in storage roots of two PFS genotypes, and to explore the relationships between anthocyanin synthesis and starch accumula-tion. [Method] A field experiment was carried out to determine the changes in yield components, yield, contents of anthocyanin and starch, activities of phenylalanine ammonia-lyase (PAL) and adenosine 5-diphosphate glucose pyrophosphorylase (AG-Pase) in two genotypes of PFS (Ipomoea batatas L., var. ‘Ayamurasaki’ and‘Jishu18’). [Result] The application of COR significantly increased starch and antho-cyanin content in storage roots of Jishu18 across developmental stages by inducing the activities of PAL and AGPase, and final y enhanced yield by promoting fresh weight of storage roots. Ayamurasaki was insensitive to treatment with COR al-though its PAL activity temporal y increased. The starch and anthocyanin content of Aya, and the anthocyanin content of Jishu18 increased progressively across devel-opmental stages with or without COR application, but the starch content of Jishu18 increased initial y, then decreased before increasing again without application of COR. Treatment with COR reduced downward trend of starch accumulation in Jishu18. Thus, the effect of COR on accumulation of anthocyanin and starch in storage roots of PFS differs according to genotypes. [Conclusion] The application of 0.05 μmol/L COR may increase starch and anthocyanin content in PFS genotypes with lower starch and anthocyanin content in storage roots.

  4. Post-harvest UVC irradiation effect on anthocyanin profile of grape berries

    Anthocyanins are a class of phenolic compounds that contribute to the color of red grapes and have shown nutraceutical properties for human health. UVC light irradiation has been proved to increase phenolic compounds such as stilbenes, but its effect on anthocyanins has not been reported. The aim of this work was to identify the best treatment conditions of UVC light irradiation on post-harvest berries of Malbec (M), Cabernet Sauvignon (CS) and Tempranillo (T) for anthocyanin increments. Grape berries were irradiated with 240 W at 20 and 40 cm from the light source, for 30, 60 and 120 seconds. Both, irradiated and control grapes were stored on darkness at 20 C degree until anthocyanin extraction with methanol/ClH. HPLC analysis were performed and nine anthocyanins were quantified. UVC light irradiation modified the anthocyanin profile of the three cultivars. All the glucoside anthocyanins derivates and peonidin-acetyl-glucoside, as well as total anthocyanins were increased when CS berries were exposed to UVC for 120 s at 40 cm. This suggests that UVC stimulated the entire biosynthetic pathway. The anthocyanin content of the control berries was always higher than the treatments with UVC on M and T, making necessary to evaluate less rigorous conditions for these varieties. (authors)

  5. UV-B-induced anthocyanin synthesis in maize regulated by FMN and inhibitors of FMN photoreactions

    Anthocyanin synthesis in maize (Zea mays L., cv. ganga safed) under white and UV-B light has been investigated after pretreatment of seedlings with flavin mononucleotide (FMN) and inhibitors of flavin photoreactions. UV-B enhanced synthesis of anthocyanin compared to white light, and this enhancement was further promoted by flavin mononucleotide (FMN). Salicyl hydroxamic acid, sodium azide and potassium iodide, which interfere with the photoreactions of flavin, inhibit UV-B-induced and FMN-promoted anthocyanin synthesis. A flavin may be involved as a photoreceptor of UV-B radiation for anthocyanin synthesis in maize

  6. Engineering the anthocyanin regulatory complex of strawberry (Fragaria vesca

    Kui eLin-Wang

    2014-11-01

    Full Text Available The woodland strawberry, Fragaria vesca is a model fruit for a number of rosaceous crops. We have engineered altered concentrations of anthocyanin in F. vesca, to determine the impact on plant growth and fruit quality. Anthocyanin concentrations were significantly increased by over-expression or decreased by knock-down of the R2R3 MYB activator, MYB10. In contrast, a potential bHLH partner for MYB10 (bHLH33 did not affect the anthocyanin pathway when knocked down using RNAi constructs. Metabolic analysis of fruits revealed that, of all the polyphenolics surveyed, only cyanidin and pelargonidin glucoside, and coumaryl hexose were significantly affected by over-expression and knock down of MYB10. Using the F. vesca genome sequence, members of the MYB, bHLH and WD40 families were examined. Global analysis of gene expression and targeted qPCR analysis of biosynthetic genes and regulators confirmed the effects of altering MYB10 expression, as well as the knock-down of bHLH33. Other members of the MYB transcription factor family were affected by the transgenes. Transient expression of strawberry genes in Nicotiana benthamiana revealed that MYB10 can auto-regulate itself, and potential repressors of MYB10. In tobacco, MYB10’s activation of biosynthetic steps is inhibited by the strawberry repressor MYB1.

  7. Engineering the anthocyanin regulatory complex of strawberry (Fragaria vesca).

    Lin-Wang, Kui; McGhie, Tony K; Wang, Mindy; Liu, Yuhui; Warren, Benjamin; Storey, Roy; Espley, Richard V; Allan, Andrew C

    2014-01-01

    The woodland strawberry, Fragaria vesca is a model fruit for a number of rosaceous crops. We have engineered altered concentrations of anthocyanin in F. vesca, to determine the impact on plant growth and fruit quality. Anthocyanin concentrations were significantly increased by over-expression or decreased by knock-down of the R2R3 MYB activator, MYB10. In contrast, a potential bHLH partner for MYB10 (bHLH33) did not affect the anthocyanin pathway when knocked down using RNAi constructs. Metabolic analysis of fruits revealed that, of all the polyphenolics surveyed, only cyanidin, and pelargonidin glucoside, and coumaryl hexose were significantly affected by over-expression and knock down of MYB10. Using the F. vesca genome sequence, members of the MYB, bHLH, and WD40 families were examined. Global analysis of gene expression and targeted qPCR analysis of biosynthetic genes and regulators confirmed the effects of altering MYB10 expression, as well as the knock-down of bHLH33. Other members of the MYB transcription factor family were affected by the transgenes. Transient expression of strawberry genes in Nicotiana benthamiana revealed that MYB10 can auto-regulate itself, and potential repressors of MYB10. In tobacco, MYB10's activation of biosynthetic steps is inhibited by the strawberry repressor MYB1. PMID:25477896

  8. Signal perception, transduction, and gene expression involved in anthocyanin biosynthesis

    Anthocyanin pigments provide fruits and flowers with their bright red and blue colors and are induced in vegetative tissues by various signals. The biosynthetic pathway probably represents one of the best‐studied examples of higher plant secondary metabolism. It has attracted much attention of plant geneticists because of the dispensable nature of the compounds it produces. Not unexpectedly, several excellent reviews on anthocyanin biosynthesis have been published over the last 5 years (Dooner et al., 1991; Martin and Gerats, 1993a, 1993b; Koes et al., 1994; Holton and Cornish, 1995). These reviews emphasize the late steps of pigment biosynthesis rather than the early and intermediate events of signal perception and transduction. This review is broader and not only covers the identification of components of the anthocyanin signal perception/transduction networks but also provides a description of our current understanding of how they evoke the responses that they do. Progress has derived from a combination of biochemical, molecular and genetic studies. We discuss a range of relevant research to highlight the different experimental approaches being used and the diverse biological systems under investigation. (author)

  9. A New Acylated Flavonoid from Anaphalis aureo-punctata

    2003-01-01

    A new acylated tlavonoid glycoside, 3-O-kaempferol-3-O-acetyl-6-O-(P-coumaroyl)-β-D-glucopyranoside 1 was isolated from the whole plant of Anaphalis aureo-punctata. The structure was established by spectral methods.

  10. Regioselective self-acylating cyclodextrins in organic solvent

    Eunae Cho; Deokgyu Yun; Daham Jeong; Jieun Im; Hyunki Kim; Dindulkar, Someshwar D.; Youngjin Choi; Seunho Jung

    2016-01-01

    Amphiphilic cyclodextrins have been synthesized with self-acylating reaction using vinyl esters in dimethylformamide. In the present study no base, catalyst, or enzyme was used, and the structural analyses using thin layer chromatography, nuclear magnetic resonance spectroscopy and mass spectrometry show that the cyclodextrin is substituted preferentially by one acyl moiety at the C2 position of the glucose unit, suggesting that cyclodextrin functions as a regioselective catalytic carbohydrat...

  11. Study on Chemical Constituents and Antioxidant Activity of Anthocyanins from Ipomoea batatas L.(purple sweet potato)%紫甘薯花色苷的组分及抗氧化活性研究

    朱洪梅; 赵猛

    2009-01-01

    Anthocyanins extracted from purple sweet potatoes (Ipomoea batatas L.) were purified through AB-8 resin column. The extract contains 11 kinds of anthocyanins by HPLC-DAD analysis. The majority of the anthocyanins are acylated cyanidin and peonidin. The objective of this study was to investigate the antioxidant activities of anthocyanins from purple sweet potatoes by different analytical methods: the α,α-diphenyl-β-picrylhydrazyl (DPPH) radical-scavenging effect and superoxide anions radical-scavenging effect, reducing power and antioxidant effect on lipid peroxidation in a linoleic acid model system. At a concentration of 0.5g/L, the reducing power of anthocyanins, L-ascorbic acid (L-AA) and butylated hydroxytoluene (BHT) reached 0.572, 0.460 and 0.121, respectively. The result displayed that anthocyanins possessed excellent reducing power. The fact that half inhibition concentrations (IC50) of anthocyanins scavenging DPPH radical and superoxide anions radical were 6.94 and 3.68mg/Lrespectively indicates that anthocyanins were effective in scavenging DPPH and superoxide anions radical. In addition, anthocyanins could significantly inhibit the peroxidation of lipid.%对紫甘薯花色苷的化学成分和抗氧化活性进行了研究.研究采用大孔树脂AB-8纯化紫甘薯花色苷,高效液相色谱-2极管阵列法(HPLC-DAD)分析表明,纯化后的提取物中共含有11种花色苷,其中主要成分为酰化的矢车菊素和芍药素.并测定了紫甘薯总花色苷在DPPH自由基清除体系、超氧阴离子体系、还原力和亚油酸体系的抗氧化活性.在质量浓度均为0.5g/L时,花色苷、L-AA和 BHT的还原力分别为0.572、0.460 和0.121,花色苷的清除DPPH自由基的半数抑制浓度(IC50)和清除超氧阴离子IC50分别为6.94和3.68mg/L,表明花色苷还原能力强,并能有效地清除DPPH自由基和超氧阴离子.此外,紫甘薯花色苷能较好地抑制脂质过氧化.

  12. Anthocyanin indexes, quercetin, kaempferol, and myricetin concentration in leaves and fruit of Abutilon theophrasti Medik. genetic resources

    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 ...

  13. AKTIVITAS ANTIOKSIDAN ANTOSIANIN BERAS KETAN HITAM SELAMA FERMENTASI [Antioxidant Activity of Anthocyanin of Black Glutinous Rice During Fermentation

    Nanik Suhartatik1)*; Muhammad Nur Cahyanto; Sri Raharjo2); Endang S Rahayu1)

    2013-01-01

    Anthocyanin is a group of bioactive compound found to be abundant in black glutinous rice. It has been widely studied for their health beneficial effect. Hydrolysis of anthocyanin glycoside into anthocyanidin and sugar by β,D-glucosidase is presumed to be the first step in anthocyanin metabolism. Enzymatic degradation of anthocyanin was reported to produce not only more stable compounds, but also healthier compounds with better bioavailability. Some species of Lactic Acid Bacteria showed β,D-...

  14. Different Localization Patterns of Anthocyanin Species in the Pericarp of Black Rice Revealed by Imaging Mass Spectrometry

    Yukihiro Yoshimura; Nobuhiro Zaima; Tatsuya Moriyama; Yukio Kawamura

    2012-01-01

    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 imag...

  15. Anthocyanin-Rich Juice Lowers Serum Cholesterol, Leptin, and Resistin and Improves Plasma Fatty Acid Composition in Fischer Rats

    Daniela Graf; Stephanie Seifert; Anke Jaudszus; Achim Bub; Bernhard Watzl

    2013-01-01

    Obesity and obesity-associated diseases e.g. cardiovascular diseases and type 2 diabetes are spread worldwide. Anthocyanins are supposed to have health-promoting properties, although convincing evidence is lacking. The aim of the present study was to investigate the effect of anthocyanins on several risk factors for obesity-associated diseases. Therefore, Fischer rats were fed anthocyanin-rich grape-bilberry juice or an anthocyanin-depleted control juice for 10 weeks. Intervention with anthoc...

  16. An R2R3 MYB transcription factor associated with regulation of the anthocyanin biosynthetic pathway in Rosaceae (on linr)

    Wang, Kui-Lin; Bolitho, Karen; Grafton, Karryn; Kortstee, A J; Karunairetnam, Sakuntala; McGhie, T.K.; Espley, R.V.; Hellens, R.P.; Allan, A.C.

    2010-01-01

    Background - The control of plant anthocyanin accumulation is via transcriptional regulation of the genes encoding the biosynthetic enzymes. A key activator appears to be an R2R3 MYB transcription factor. In apple fruit, skin anthocyanin levels are controlled by a gene called MYBA or MYB1, while the gene determining fruit flesh and foliage anthocyanin has been termed MYB10. In order to further understand tissue-specific anthocyanin regulation we have isolated orthologous MYB genes from all th...

  17. Arabidopsis acyl-acyl carrier protein synthetase AAE15 with medium chain fatty acid specificity is functional in cyanobacteria

    Kaczmarzyk, Danuta; Hudson, Elton P.; Fulda, Martin

    2016-01-01

    Cyanobacteria are potential hosts for the biosynthesis of oleochemical compounds. The metabolic precursors for such compounds are fatty acids and their derivatives, which require chemical activation to become substrates in further conversion steps. We characterized the acyl activating enzyme AAE15 of Arabidopsis encoded by At4g14070, which is a homologue of a cyanobacterial acyl-ACP synthetase (AAS). We expressed AAE15 in insect cells and demonstrated its AAS activity with medium chain fatty ...

  18. Different localization patterns of anthocyanin species in the pericarp of black rice revealed by imaging mass spectrometry.

    Yukihiro Yoshimura

    Full Text Available 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.

  19. CCoAOMT down-regulation activates anthocyanin biosynthesis in petunia

    N.F.M. Shaipulah; J.K. Muhlemann; B.D. Woodworth; A. Van Moerkercke; J.C. Verdonk; A.M. Ramirez; M.A. Haring; N. Dudareva; R.C. Schuurink

    2015-01-01

    Anthocyanins and volatile phenylpropenes (isoeugenol and eugenol) in petunia flowers have the precursor 4-coumaryl CoA in common. These phenolics are produced at different stages during flower development. Anthocyanins are synthesized during early stages of flower development and sequestered in vacu

  20. Issues with fruit dietary supplements in the US - authentication by anthocyanin

    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...

  1. Rosaceae products: Anthocyanin quality and comparisons between dietary supplements and foods

    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...

  2. CCoAOMT down-regulation activates anthocyanin biosynthesis in petunia

    Shaipulah, N.F.M.; Muhlemann, Joëlle K.; Woodworth, Benjamin D.; Moerkercke, Van Alex; Verdonk, J.C.; Ramirez, A.A.; Haring, Michel A.; Dudareva, Natalia; Schuurink, Robert C.

    2016-01-01

    Anthocyanins and volatile phenylpropenes (isoeugenol and eugenol) in petunia (Petunia hybrida) flowers have the precursor 4-coumaryl coenzyme A (CoA) in common. These phenolics are produced at different stages during flower development. Anthocyanins are synthesized during early stages of flower d

  3. Using gamma irradiation for the recovery of anthocyanins from grape pomace

    Ayed, N.; Yu, H.-L.; Lacroix, M. E-mail: Monique_Lacroix@iaf.uquebec.ca

    2000-03-01

    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. (author)

  4. Matrix Effects on the Stability and Antioxidant Activity of Red Cabbage Anthocyanins under Simulated Gastrointestinal Digestion

    Anna Podsędek

    2014-01-01

    Full Text Available 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.

  5. Genetic analyses of anthocyanin concentrations and the intensity of red color in onion

    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...

  6. Using gamma irradiation for the recovery of anthocyanins from grape pomace

    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. (author)

  7. Effect of calcium on strawberry fruit flavonid gene expression and anthocyanins accumulation

    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...

  8. Health Benefits of Anthocyanins and Their Encapsulation for Potential Use in Food Systems: A Review.

    Yousuf, Basharat; Gul, Khalid; Wani, Ali Abas; Singh, Preeti

    2016-10-01

    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. PMID:25745811

  9. Anthocyanin and Potential Therapeutic Traits in Clitoria, Desmodium, Corchorus, Catharanthus, and Hibiscus Species

    The USDA, ARS, Plant Genetic Resources Conservation Unit curates several important nutraceutical and medicinal plant species. Anthocyanins are responsible for flower, leaf, seed coat color in plants, and are antioxidants as well. However, little is known about anthocyanin content in Clitoria terna...

  10. Using gamma irradiation for the recovery of anthocyanins from grape pomace

    Ayed, N.; Yu, H.-L.; Lacroix, M.

    2000-03-01

    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.

  11. Molecular mechanism for cadmium-induced anthocyanin accumulation in Azolla imbricata.

    Dai, Ling-Peng; Dong, Xin-Jiao; Ma, Hai-Hu

    2012-04-01

    Anthocyanins inducibly synthesized by Cd treatment showed high antioxidant activity and might be involved in internal detoxification mechanisms of Azolla imbricata against Cd toxicity. In order to understand anthocyanin biosynthesis mechanism during Cd stress, the cDNAs encoding chalcone synthase (CHS) and dihydroflavonol reductase (DFR), two key enzymes in the anthocyanin synthesis pathway, were isolated from A. imbricata. Deduced amino acid sequences of the cDNAs showed high homology to the sequences from other plants. Expression of AiDFR, and to a lesser extent AiCHS, was significantly induced in Cd treatment plant in comparison with the control. CHS and DFR enzymatic activities showed similar pattern changes with these genes expression during Cd stress. These results strongly indicate that Cd induced anthocyanin accumulation is probably mediated by up-regulation of structural genes including CHS and DFR, which might further increase the activities of enzymes encoded by these structural genes that control the anthocyanin biosynthetic steps. PMID:22225708

  12. Absorption and excretion of black currant anthocyanins in human and Watanabe Heritable Hyperlipidemic rabbits

    Nielsen, I. L.. F.; Ravn-Haren, Gitte; Dragsted, L. O.;

    2003-01-01

    Anthocyanins are thought to protect against cardiovascular diseases. Watanabe heritable hyperlipidemic (WHHL) rabbits are hypercholesterolemic and used as a model of the development of atherosclerosis. To compare the uptake and excretion of anthocyanins in humans and WHHL rabbits, single-dose black...... currant anthocyanin studies were performed. Procedures for workup and analyses of urine and plasma samples containing anthocyanins were developed with high recoveries (99 and 81%, respectively) and low limits of quantification (greater than or equal to 6.6 and greater than or equal to 1.1 nM, respectively......). The excretion and absorption of anthocyanins from black currant juice were found to be within the same order of magnitude in the two species regarding urinary excretion within the first 4 h (rabbits, 0.035%; humans, 0.072%) and t(ma)x (rabbits, similar to30 min; humans, similar to45 min). A food...

  13. Anthocyanins in purple and blue wheat grains and in resulting bread: quantity, composition, and thermal stability.

    Bartl, Pavel; Albreht, Alen; Skrt, Mihaela; Tremlová, Bohuslava; Ošťádalová, Martina; Šmejkal, Karel; Vovk, Irena; Ulrih, Nataša Poklar

    2015-01-01

    The anthocyanin composition of blue (Triticum aestivum L., cv. Skorpion) and purple wheat (Triticum aethiopicum JAKUBZ cv. Abyssinskaja arrasajta cv. Abyssinskaja arrasajta), cultivated in the Czech Republic, and of the prepared whole blue and purple wheat bread was determined. In blue and purple wheat, 19 and 26 anthocyanins, respectively, were tentatively identified by liquid chromatography and mass spectrometry. The total content of anthocyanins determined in blue and purple wheat was 9.26 and 13.23 mgkg(-1), respectively. The breads were baked at 240 and 180 °C. Some significant differences in anthocyanins content were observed between breads prepared at different baking temperatures. The content of cyanidin-3-glucoside, delphinidin-3-glucoside and pelargonidin-3-glucoside was determinated in starting material, whole meal flours and baked breads. These kinds of wheat are suitable for baking bread, since intake of anthocyanins may play an important role in the prevention of human diseases. PMID:26088282

  14. Regioselective Acylation of Diols and Triols: The Cyanide Effect.

    Peng, Peng; Linseis, Michael; Winter, Rainer F; Schmidt, Richard R

    2016-05-11

    Central topics of carbohydrate chemistry embrace structural modifications of carbohydrates and oligosaccharide synthesis. Both require regioselectively protected building blocks that are mainly available via indirect multistep procedures. Hence, direct protection methods targeting a specific hydroxy group are demanded. Dual hydrogen bonding will eventually differentiate between differently positioned hydroxy groups. As cyanide is capable of various kinds of hydrogen bonding and as it is a quite strong sterically nondemanding base, regioselective O-acylations should be possible at low temperatures even at sterically congested positions, thus permitting formation and also isolation of the kinetic product. Indeed, 1,2-cis-diols, having an equatorial and an axial hydroxy group, benzoyl cyanide or acetyl cyanide as an acylating agent, and DMAP as a catalyst yield at -78 °C the thermodynamically unfavorable axial O-acylation product; acyl migration is not observed under these conditions. This phenomenon was substantiated with 3,4-O-unproteced galacto- and fucopyranosides and 2,3-O-unprotected mannopyranosides. Even for 3,4,6-O-unprotected galactopyranosides as triols, axial 4-O-acylation is appreciably faster than O-acylation of the primary 6-hydroxy group. The importance of hydrogen bonding for this unusual regioselectivity could be confirmed by NMR studies and DFT calculations, which indicate favorable hydrogen bonding of cyanide to the most acidic axial hydroxy group supported by hydrogen bonding of the equatorial hydroxy group to the axial oxygen. Thus, the "cyanide effect" is due to dual hydrogen bonding of the axial hydroxy group which enhances the nucleophilicity of the respective oxygen atom, permitting an even faster reaction for diols than for mono-ols. In contrast, fluoride as a counterion favors dual hydrogen bonding to both hydroxy groups leading to equatorial O-acylation. PMID:27104625

  15. Synthesis of N-acyl-2-amino-2-deoxy-[1-14C]-glucoses as precursors for the biosynthesis of novel N-acyl-neuraminic acids

    N-Propanoyl-, N-butanoyl-, N-pentanoyl-, N-hexanoyl-, N-heptanoyl-, and N-crotonoyl-[1-14]C -D-glucosamine were synthesized from [1-14C]-D-glucosamine and their respective carbonic acid anhydrides as precursors for the biosynthesis of the corresponding N-acyl neuraminic acids. The N-acyl-glucosamines are phosphorylated to their respective phosphate by N-acetyl-glucosamine kinase in a rat liver homogenate. These precursors may become valuable tools to investigate the biological role of the N-acyl side chain of N-acyl-glucosamines and N-acyl neuraminic acids which are components of glycoconjugates. (Author)

  16. Control of anthocyanin and non-flavonoid compounds by anthocyanin-regulating MYB and bHLH transcription factors in Nicotiana benthamiana leaves

    Outchkourov, Nikolay S.; Carollo, Carlos A.; Gomez-Roldan, Victoria; De Vos, Ric C. H.; Bosch, Dirk; Hall, Robert D.; Beekwilder, Jules

    2014-01-01

    Coloration of plant organs such as fruit, leaves and flowers through anthocyanin production is governed by a combination of MYB and bHLH type transcription factors (TFs). In this study we introduced Rosea1 (ROS1, a MYB type) and Delila (DEL, a bHLH type), into Nicotiana benthamiana leaves by agroinfiltration. ROS1 and DEL form a pair of well-characterized TFs from Snapdragon (Antirrhinum majus), which specifically induce anthocyanin accumulation when expressed in tomato fruit. In N. benthamia...

  17. Functional conservation analysis and expression modes of grape anthocyanin synthesis genes responsive to low temperature stress.

    Zhang, Cheng; Jia, Haifeng; Wu, Weimin; Wang, Xicheng; Fang, Jinggui; Wang, Chen

    2015-12-10

    In grape cultivation, low temperature generally increases the expression of genes involved in synthesis of anthocyanin. In this study, multi-type structural analysis of the proteins encoded by five anthocyanin biosynthesis genes VvF3H, VvPAL, VvCHS3, VvCHS2 and VvLDOX, in addition to nine of their homologous genes revealed that proteins in grapevine shared a high similarity with that in kiwi, red orange and some other species in which the biosynthesis of anthocyanin significantly influenced by low temperature as proved by previous studies. Low temperature regulatory elements were also found in the promoter region of the grapevine genes VvCHS2, VvPAL and VvF3H. These findings indicate that the functions of anthocyanin biosynthesis genes in grapevine are conservative and might be sensitive to low temperature. In order to identify the specific expression patterns of the five anthocyanin biosynthesis genes and the changes of polyphenols, anthocyanins and flavonoids under low temperature stress. The transcription analysis of the five genes and the content of polyphenols, anthocyanins and flavonoids in grape skins were examined, by using Vitis vinifera L. cv. 'Yongyou 1' and 'Juxing' berries as experimental material and treated at 4°C and 25°C for 24h, 48 h, 72 h and 96 h. The results showed that low temperature greatly enhanced the expression of the five anthocyanin biosynthesis genes. Low temperature greatly slowed down the decomposition of polyphenol, anthocyanin, and flavonoid in grape skins. Our study also found that cv. 'Juxing' responded more sensitively to low temperature than cv. 'Yongyou 1'. All the findings would provide a basis for further study on the mechanism of anthocyanin biosynthesis under environmental stress. PMID:26253159

  18. A gene-derived SNP-based high resolution linkage map of carrot including the location of QTL conditioning root and leaf anthocyanin pigmentation

    Cavagnaro, Pablo F; Iorizzo, Massimo; Yildiz, Mehtap; Senalik, Douglas; Parsons, Joshua; Ellison, Shelby; Simon, Philipp W

    2014-01-01

    Background Purple carrots accumulate large quantities of anthocyanins in their roots and leaves. These flavonoid pigments possess antioxidant activity and are implicated in providing health benefits. Informative, saturated linkage maps associated with well characterized populations segregating for anthocyanin pigmentation have not been developed. To investigate the genetic architecture conditioning anthocyanin pigmentation we scored root color visually, quantified root anthocyanin pigments by...

  19. Regioselective self-acylating cyclodextrins in organic solvent

    Cho, Eunae; Yun, Deokgyu; Jeong, Daham; Im, Jieun; Kim, Hyunki; Dindulkar, Someshwar D.; Choi, Youngjin; Jung, Seunho

    2016-03-01

    Amphiphilic cyclodextrins have been synthesized with self-acylating reaction using vinyl esters in dimethylformamide. In the present study no base, catalyst, or enzyme was used, and the structural analyses using thin layer chromatography, nuclear magnetic resonance spectroscopy and mass spectrometry show that the cyclodextrin is substituted preferentially by one acyl moiety at the C2 position of the glucose unit, suggesting that cyclodextrin functions as a regioselective catalytic carbohydrate in organic solvent. In the self-acylation, the most acidic OH group at the 2-position and the inclusion complexing ability of cyclodextrin were considered to be significant. The substrate preference was also observed in favor of the long-chain acyl group, which could be attributed to the inclusion ability of cyclodextrin cavity. Furthermore, using the model amphiphilic building block, 2-O-mono-lauryl β-cyclodextrin, the self-organized supramolecular architecture with nano-vesicular morphology in water was investigated by fluorescence spectroscopy, dynamic light scattering and transmission electron microscopy. The cavity-type nano-assembled vesicle and the novel synthetic methods for the preparation of mono-acylated cyclodextrin should be of great interest with regard to drug/gene delivery systems, functional surfactants, and carbohydrate derivatization methods.

  20. Determination of Anthocyanin in Merlot Grape and Wine by HPLC Method%HPLC法测定梅鹿辄葡萄与葡萄酒中的花色素苷

    莫寅斌

    2012-01-01

    [Objective] The aim was to research the determination of the anthocyanin component and its relative content in the merlot grape and the grape wine by HPLC method. [ Method] The anthocyanin in the brewing grape merlot was extracted by using the ethanol and the anthocyanin in the merlot grape and the grape wine were determined by the HPLC method respectively, [ Result ] Among 9 kinds of anthocyanin determined in the merlot grape fruits and wine, the malvidin 3-0-glucoside had the highest anthocyanin content, being 28.41% and 54.00% of total ingredients. In the fruits, the malvidin 3-O-(6-O-acetyl) glucoside and the malvidin 3-O-(6-O-p-p-coumaric acyl) glucoside were 22.16% and 25.28% , which was consisted of the main anthocyanin, while in the grape wine, these 2 kinds of anthocyanin contents decreased rapidly to 4.32% and 11. 88% , which weren' t the main color-generation component of the merlot grape wine. [ Conclusion ] The changes of the anthocyanin during the transformation process from the merlot grape berries to the grape wine were analyzed preliminarily, which provided the basis for the objective appraisal on the grape variety and other researches.%[目的]利用HPLC法对梅鹿辄葡萄和葡萄酒中的花色素苷组分及其相对含量进行研究.[方法]利用乙醇提取酿酒葡萄梅鹿辄中的花色素苷,并用HPLC法分别测定梅鹿辄葡萄及葡萄酒中的花色素苷.[结果]在梅鹿辄葡萄果实及葡萄酒中测得的9种花色素苷中,均以二甲花翠素3-O-葡萄糖苷含量最高,分别占总成分的28.41%和54.00%;在果实中二甲花翠素3-O-(6-O-乙酰)葡萄糖苷、二甲花翠素3-O-(6-O-对香豆酰)葡萄糖苷分别以22.16%和25.28%的含量构成主要花色素苷,而在葡萄酒中这两种花色素苷含量迅速下降,分别降至4.32%;11.88%,不是梅鹿辄葡萄酒中的主要呈色成分.[结论]初步分析了花色素苷在梅鹿辄葡萄浆果向葡萄酒转变过程中的变化,为客观

  1. Trapping of the Enoyl-Acyl Carrier Protein Reductase-Acyl Carrier Protein Interaction.

    Tallorin, Lorillee; Finzel, Kara; Nguyen, Quynh G; Beld, Joris; La Clair, James J; Burkart, Michael D

    2016-03-30

    An ideal target for metabolic engineering, fatty acid biosynthesis remains poorly understood on a molecular level. These carrier protein-dependent pathways require fundamental protein-protein interactions to guide reactivity and processivity, and their control has become one of the major hurdles in successfully adapting these biological machines. Our laboratory has developed methods to prepare acyl carrier proteins (ACPs) loaded with substrate mimetics and cross-linkers to visualize and trap interactions with partner enzymes, and we continue to expand the tools for studying these pathways. We now describe application of the slow-onset, tight-binding inhibitor triclosan to explore the interactions between the type II fatty acid ACP from Escherichia coli, AcpP, and its corresponding enoyl-ACP reductase, FabI. We show that the AcpP-triclosan complex demonstrates nM binding, inhibits in vitro activity, and can be used to isolate FabI in complex proteomes. PMID:26938266

  2. Cholinesterase catalyzed hydrolysis of O-acyl derivatives of serotonin

    Hydrolysis of O acyl serotonin derivatives containing the residues of monocarbon dicarbon and amino acids under the effect of horse serum butyryl cholinesterase and bull erythrocytic acetylcholinesterase has been studied. It has been established, that acetylcholinesterase hydrolizes O acetylserotonin only; butyrylcholinesterase hydrolizes all the compounds investigated, except for 5,5'-terephthaloildioxytriptamine. The kinetic parameters of hydrolysis were determined. O acyl serotonin derivatives turned out good substrates of butylrylcholinesterase; serotonin and 5.5'-terephtaloildioxytriptamine are effective competitine inhibitors of the enzyme. Estimating of resistance of O acyl serotonin derivatines to blood cholinesterase effect under physiological conditions shows that the compounds investigated with the exception of 5,5'-terephthaloildioxytriptamine must be quickly hydrolyzed under butyrylcholinesterase action. 5,5'-terephthaloildioxytriptamine is suggested as a radioprotective preparation with the prolonged effect, which agrees with the biological test results

  3. Ghrelin O-Acyl Transferase: Bridging Ghrelin and Energy Homeostasis

    Andrew Shlimun

    2011-01-01

    Full Text Available Ghrelin O-acyl transferase (GOAT is a recently identified enzyme responsible for the unique n-acyl modification of ghrelin, a multifunctional metabolic hormone. GOAT structure and activity appears to be conserved from fish to man. Since the acyl modification is critical for most of the biological actions of ghrelin, especially metabolic functions, GOAT emerged as a very important molecule of interest. The research on GOAT is on the rise, and several important results reiterating its significance have been reported. Notable among these discoveries are the identification of GOAT tissue expression patterns, effects on insulin secretion, blood glucose levels, feeding, body weight, and metabolism. Several attempts have been made to design and test synthetic compounds that can modulate endogenous GOAT, which could turn beneficial in favorably regulating whole body energy homeostasis. This paper will focus to provide an update on recent advances in GOAT research and its broader implications in the regulation of energy balance.

  4. Estimation of Anthocyanin Content of Berries by NIR Method

    Zsivanovits, G.; Ludneva, D.; Iliev, A.

    2010-01-01

    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.

  5. Estimation of Anthocyanin Content of Berries by NIR Method

    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.

  6. Antioxidant Activity and Acetylcholinesterase Inhibition of Grape Skin Anthocyanin (GSA

    Mehnaz Pervin

    2014-07-01

    Full Text Available We aimed to investigate the antioxidant and acetylcholinesterase inhibitory activities of the anthocyanin rich extract of grape skin. Grape skin anthocyanin (GSA neutralized free radicals in different test systems, such as 2,-2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS and 2,2-diphenyl-1-picrylhydrazyl (DPPH assays, to form complexes with Fe2+ preventing 2,2'-azobis(2-amidinopropane dihydrochloride (AAPH-induced erythrocyte hemolysis and oxidative DNA damage. Moreover, GSA decreased reactive oxygen species (ROS generation in isolated mitochondria thus inhibiting 2',-7'-dichlorofluorescin (DCFH oxidation. In an in vivo study, female BALB/c mice were administered GSA, at 12.5, 25, and 50 mg per kg per day orally for 30 consecutive days. Herein, we demonstrate that GSA administration significantly elevated the level of antioxidant enzymes in mice sera, livers, and brains. Furthermore, GSA inhibited acetylcholinesterase (AChE in the in vitro assay with an IC50 value of 363.61 µg/mL. Therefore, GSA could be an excellent source of antioxidants and its inhibition of cholinesterase is of interest with regard to neurodegenerative disorders such as Alzheimer’s disease.

  7. Caveolar fatty acids and acylation of caveolin-1.

    Qian Cai

    Full Text Available PURPOSE: Caveolae are cholesterol and sphingolipids rich subcellular domains on plasma membrane. Caveolae contain a variety of signaling proteins which provide platforms for signaling transduction. In addition to enriched with cholesterol and sphingolipids, caveolae also contain a variety of fatty acids. It has been well-established that acylation of protein plays a pivotal role in subcellular location including targeting to caveolae. However, the fatty acid compositions of caveolae and the type of acylation of caveolar proteins remain largely unknown. In this study, we investigated the fatty acids in caveolae and caveolin-1 bound fatty acids. METHODS: Caveolae were isolated from Chinese hamster ovary (CHO cells. The caveolar fatty acids were extracted with Folch reagent, methyl esterificated with BF3, and analyzed by gas chromatograph-mass spectrometer (GC/MS. The caveolin-1 bound fatty acids were immunoprecipitated by anti-caveolin-1 IgG and analyzed with GC/MS. RESULTS: In contrast to the whole CHO cell lysate which contained a variety of fatty acids, caveolae mainly contained three types of fatty acids, 0.48 µg palmitic acid, 0.61 µg stearic acid and 0.83 µg oleic acid/caveolae preparation/5 × 10(7 cells. Unexpectedly, GC/MS analysis indicated that caveolin-1 was not acylated by myristic acid; instead, it was acylated by palmitic acid and stearic acid. CONCLUSION: Caveolae contained a special set of fatty acids, highly enriched with saturated fatty acids, and caveolin-1 was acylated by palmitic acid and stearic acid. The unique fatty acid compositions of caveolae and acylation of caveolin-1 may be important for caveolae formation and for maintaining the function of caveolae.

  8. Fluorescently labelled bovine acyl-CoA-binding protein acting as an acyl-CoA sensor: interaction with CoA and acyl-CoA esters and its use in measuring free acyl-CoA esters and non-esterified fatty acids

    Wadum, M.C.; Villadsen, J.K.; Feddersen, S.;

    2002-01-01

    Long-chain acyl-CoA esters are key metabolites in lipid synthesis and b-oxidation but, at the same time, are important regulators of intermediate metabolism, insulin secretion, vesicular trafficking and gene expression. Key tools in studying the regulatory functions of acyl-CoA esters are reliable...... methods for the determination of free acyl-CoA concentrations. No such method is presently available. In the present study, we describe the synthesis of two acyl-CoA sensors for measuring free acyl-CoA concentrations using acyl-CoA-binding protein as a scaffold. Met24 and Ala53 of bovine acyl......-CoA-binding protein were replaced by cysteine residues, which were covalently modified with 6-bromoacetyl-2-dimethylaminonaphthalene to make the two fluorescent acyl-CoA indicators (FACIs) FACI-24 and FACI-53. FACI-24 and FACI-53 showed fluorescence emission maximum at 510 and 525nm respectively, in the absence of...

  9. Anthocyanin Concentration of “Assaria” Pomegranate Fruits During Different Cold Storage Conditions

    Graça Miguel

    2004-01-01

    Full Text Available The concentration of anthocyanins in fruits of “Assaria” pomegranate, a sweet Portuguese cultivar typically grown in Algarve (south Portugal, was monitored during storage under different conditions. The fruits were exposed to cold storage (5∘C after the following treatments: spraying with wax; spraying with 1.5% CaCl2; spraying with wax and 1.5% CaCl2; covering boxes with 25 μc thickness low-density polyethylene film. Untreated fruits were used as a control. The anthocyanin levels were quantified by either comparison with an external standard of cyanidin 3-rutinoside (based on the peak area or individual calculation from the peak areas based on standard curves of each anthocyanin type. The storage time as well as the fruit treatment prior to storage influenced total anthocyanin content. The highest levels were observed at the end of the first month of storage, except for the fruits treated with CaCl2, where the maximal values were achieved at the end of the second month. The anthocyanin quantification method influenced the final result. When total anthocyanin was calculated as a sum of individual pigments quantified based on standard curves of each anthocyanin type, lower values were obtained.

  10. Anthocyanin Accumulation Mediated by Blue Light and Cytokinin in Arabidopsis Seedlings

    2006-01-01

    It has been reported that pigmentation in plants is stimulated by light and cytokinin (CTK); however, the signaling pathways and the relationship between light and CTK involved in the regulation of anthocyanin accumulation remain to be elucidated. We investigated (i) the role of blue light (BL) and CTK in anthocyanin accumulation; and (ii) the relationship between BL and CTK in wild type (WT) and hy4 mutants of Arabidopsis thaliana. Two-d-old seedlings grown on medium with or without kinetin (KT) or zeatin (ZT) in darkness were irradiated using BL at different fluence rates for 3 d before the anthocyanin content was determined using a spectrophotometric method. Anthocyanin accumulation was strongly induced by BL in WT seedlings but not in hy4 seedlings, which demonstrated that CRY1 is the main photoreceptor for BL. Both KT and ZT enhanced the response of the WT seedlings to BL in a dose-dependent manner, whereas they were not sufficient to promote anthocyanin accumulation in darkness. In addition, data from experiments using the hy4 mutant showed that the CTK effect of BL was also CRY1-dependent. The results from experiments with three different treatment programs showed that the relationship between BL and KT in anthocyanin accumulation of Arabidopsis seedlings seems neither multiplicative nor additive coaction, but rather interaction. BL is necessary for anthocyanin accumulation, and KT might be involved in the BL signaling pathway.

  11. Antioxidations and Their Correlations with Total Flavones and Anthocyanin Contents in Different Black Rice Varieties

    2005-01-01

    The antioxidations and their correlations with total flavones and anthocyanin contents in different black rice varieties were studied. The results indicated that the great differences in total antioxidant capacity (TAC), scavenging free radical capacity (SFRC), total flavones and anthocyanin contents existed among 242 black rice varieties. Comparisons of TAC,SFRC, total flavones and anthocyanin contents of different black rice types showed that the differences between black rice and white rice, indica one and japonica one, and nonglutinous one and glutinous one were significant at 0.01 levels,respectively. This showed that the TAC, SFRC, total flavones and anthocyanin contents of japonica type were higher than those of indica one, and nonglutinous type were higher than glutinous one. According to the fast clustering procedure, 242 black rice varieties could be clustered into 10 clusters, 184 indica rice varieties into 10 clusters, and 58japonica rice varieties into 6 clusters. Most significant (P<0.01) correlations existed between TAC and total flavones and anthocyanin contents, and between SFRC and total flavones and anthocyanin contents of black rice, respectively. This showed that the antioxidation of black rice was closely correlated with its active compositions of flavones and anthocyanin.

  12. Effect of Light on Anthocyanin Levels in Submerged, Harvested Cranberry Fruit

    Zhou Yu

    2004-01-01

    Full Text Available 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 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.

  13. Anthocyanins and flavonols are responsible for purple color of Lablab purpureus (L.) sweet pods.

    Cui, Baolu; Hu, Zongli; Zhang, Yanjie; Hu, Jingtao; Yin, Wencheng; Feng, Ye; Xie, Qiaoli; Chen, Guoping

    2016-06-01

    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. PMID:26995313

  14. Investigation of the kinetics of acyl group exchange Part 3

    Acyl group exchange of substituted phenyl acetates with acetic-1-14C acid catalyzed by pyridine in different solvents was followed kinetically. Structure reactivity relationship and reaction pathway for acyl exchange with acetic acid and acetic anhydride as well as for acetate catalyzed hydrolysis of substituted phenyl acetates are comparatively discussed. The radioactivity was measured by a Tricarb Scintillation Spectrophotometer [Packard Instrument Co]. The IR spectra were recorded on a UR-10 spectrophotometer. Conductrometric and dielectrometric measurements were carried out by using Radelkis equipments. Exchange rates have been calculated from the McKay equation. (F.Gy.)

  15. Funktionelle Analysen zum Acyl-CoA-Bindeprotein (ACBP)

    Klausz, Katja

    2009-01-01

    Das Fettsäurebindeprotein mit der höchsten Spezifität für langkettige, Acyl-CoA ist das Acyl-CoA-Bindeprotein (ACBP). Der Vergleich transgener, ACBP-überexprimierender Ratten mit Wildtypen nach einmonatiger Fütterung einer Niedrig- (LFD) bzw. Hochfettdiät (HFD) zeigt bei den transgenen Tieren höhere Konzentrationen an freien Fettsäuren und Triglyzeriden, sowie veränderte Glukose- und Insulinwerte. Zudem führt die ACBP-Überexpression unter LFD in der Leber zur verringerten SREBP-1c- und L-FABP...

  16. Studies on acylation of lysolecithin in chicken intestine

    The enzymatic acylation of lysolecithin to lecithin is shown to occur in the brush border-free particulate fraction of the small intestines of neonatal chicken. It requires ATP, coenzyme A and Mg2+ or Mn2+ for maximal activity. The system is specific for oleic acid. The fatty acid composition at the α-position of lysolecithin does not seem to influence the rate of acylation. The fatty acid incorporated into lysolecithin is shown to occupy exclusively, the β-position. [32P]lecithin and [1-14C]oleic acid has been used as tracers in the studies. (author)

  17. Arabidopsis ROOT HAIR DEFECTIVE3 is involved in nitrogen starvation-induced anthocyanin accumulation

    Jing Wang; Yan Wang; Ju Yang; Chunli Ma; Ying Zhang; Ting Ge; Zhi Qi; Yan Kang

    2015-01-01

    Anthocyanin accumulation is a common phenom-enon seen in plants under environmental stress. In this study, we identified a new allele of ROOT HAIR DEFECTIVE3 (RHD3) showing an anthocyanin overaccumulation phenotype under nitrogen starvation conditions. It is known that ethylene negatively regulates light- and sucrose-induced anthocyanin biosynthesis. We hypothesized that RHD3 achieves its negative effect on anthocyanin biosynthesis via an ethylene-regulating pathway. In support of this, similar to rhd3 mutants, the Arabidopsis ethylene signaling mutants etr1, ein2, and ein3/eil1 showed an anthocyanin overaccumulation phenotype under nitrogen starvation conditions. The ethylene precursor ACC strongly suppressed anthocyanin accumulation, dependent on ETR1, EIN2, EIN3/EIL1, and, partially, RHD3. In addition, inactivating RHD3 partially reversed the suppressive effect of ETO1 inactivation-evoked endogenous ethylene production on anthocyanin accumulation. The expression of nitrogen starva-tion-induced anthocyanin biosynthesis genes was negatively regulated by RHD3, but ethylene response genes were positively regulated by RHD3. Wild-type seedlings overexpress-ing RHD3 showed similar phenotypes to rhd3 mutants, indicating the existence of a fine-tuned relationship between gene expression and function. RHD3 was initial y identified as a gene involved in root hair development. This study uncovered a new physiological function of RHD3 in nitrogen starvation-induced anthocyanin accumulation and ethylene homeostasis. Correction added on 6 August 2015, after first online publica-tion:“RND3”corrected to“RHD3”.

  18. Lipopolysaccharides with acylation defects potentiate TLR4 signaling and shape T cell responses

    A Martirosyan; Ohne, Y. (Yoichiro); Degos, C. (Clara); Gorvel, L. (Laurent); Moriyon, I; Oh, S.; Gorvel, J P

    2013-01-01

    Lipopolysaccharides or endotoxins are components of Gram-negative enterobacteria that cause septic shock in mammals. However, a LPS carrying hexa-acyl lipid A moieties is highly endotoxic compared to a tetra-acyl LPS and the latter has been considered as an antagonist of hexa-acyl LPS-mediated TLR4 signaling. We investigated the relationship between the structure and the function of bacterial LPS in the context of human and mouse dendritic cell activation. Strikingly, LPS with acylation defec...

  19. Induction of anthocyanins accumulation by methyl jasmonate in shoots of Crassula multicava Lam.

    Marian Saniewski

    2012-12-01

    Full Text Available In Crassula multicava Lam. anthocyanins are formed naturally mostly in the stem near nodes and only traces in other parts of internodes. Methyl jasmonate (JA-Me applied in lanolin paste at concentrations of 0.05, 0.1, 0.5 and 1.0% on the middle part of internodes greatly stimulated anthocyanins accumulation in the internodes and in the nodes of Crassula multicava. The stimulatory effect was higher in younger tissues of the Crassula multicava stem than in older ones, and depends on the used concentration of JA-Me. The possible role of jasmonates on anthocyanins formation in Crassula multicava is discussed.

  20. Identification and characterization of seed-specific transcription factors regulating anthocyanin biosynthesis in black rice

    Kim, C.-K; Cho, M.-A.; Choi, Y.-H.; Kim, J.-A.; Kim, Y.-H.; Kim, Y.-K.; Park, S.-H

    2011-01-01

    Black rice is rich in anthocyanin and is expected to have more healthful dietary potential than white rice. We assessed expression of anthocyanin in black rice cultivars using a newly designed 135 K Oryza sativa microarray. A total of 12,673 genes exhibited greater than 2.0-fold up- or down-regulation in comparisons between three rice cultivars and three seed developmental stages. The 137 transcription factor genes found to be associated with production of anthocyanin pigment were classified ...

  1. Dynamics of anthocyanin in aging of ipomea purpurea flowers treated by uv-b radiation

    Анастасія Миколаївна Берестяна

    2014-01-01

    The dynamics of the anthocyanin content reduction in the course of aging of the Ipomoea purpureа petals, which characterizes the rate of the degradation processes in a cell, has been studied. The analysis included the impact of various UV-B radiation doses on the rate of anthocyanin age-related decomposition. The experiment proved that but one dose – 12.6 kJ/m2 contributed to the deceleration of the anthocyanin decomposition rate, within the range studied. The probable mechanisms that connect...

  2. ANTHOCYANIN PIGMENTATION IN TRITICUM AESTIVUM L.: GENETIC BASIS AND ROLE UNDER ABIOTIC STRESS CONDITIONS

    Tereshchenko O.Yu.

    2012-08-01

    Full Text Available Anthocyanins are secondary metabolites of plants. They have a wide range of biological activity such as antioxidant, photoprotection, osmoregulation, heavy metal ions chelation, antimicrobial and antifungal activities, which help plants to survive under different stress conditions. Bread wheat (T. aestivum L. can have purple pigmentation provided by anthocyanin compounds in different organs, such as grain pericarp, coleoptile, culm, leaf blades, leaf sheaths, glumes and anthers. However, the genetic mechanisms underlying formation of these traits as well as contribution of the pigmentation to stress tolerance have not been widely studied in wheat. The aim of the current study was to investigate molecular-genetic mechanisms underlying anthocyanin pigmentation in different wheat organs and to estimate the role of the pigmentation under different abiotic stress conditions in wheat seedlings. In the current study, near-isogenic lines (NILs: cv. ‘Saratovskaya 29’ (‘S29’ and lines i:S29Pp1Pp2PF and i:S29Pp1Pp3P developed on the ‘S29’ background but having grain pericarp coloration (genes Pp and more intense coleoptile (Rc, culm (Pc, leaf blade (Plb, leaf sheath (Pls pigmentation in comparison with ‘S29’, were used. Comparative transcriptional analysis of the five structural genes Chs, Chi, F3h, Dfr, Ans, encoding enzymes participating in the anthocyanin biosynthesis, was performed in different organs of NILs. It was shown that the presence of the Rc, Pc, Plb, Pls and Pp alleles conferring strong anthocyanin pigmentation induced more intense transcription of the structural genes, suggesting the genes Rc, Pc, Plb, Pls and Pp to play a regulatory role in anthocyanin biosynthesis network. To evaluate the role of anthocyanins in stress response at the seedling stage, growth ability of the NILs and anthocyanin content in their coleoptiles were assessed after treatments with NaCl (100 and 200 mM, CdCl2 (25 and 50 μM and 15% PEG 6000

  3. Dynamics of anthocyanin in aging of ipomea purpurea flowers treated by uv-b radiation

    Анастасія Миколаївна Берестяна

    2014-10-01

    Full Text Available The dynamics of the anthocyanin content reduction in the course of aging of the Ipomoea purpureа petals, which characterizes the rate of the degradation processes in a cell, has been studied. The analysis included the impact of various UV-B radiation doses on the rate of anthocyanin age-related decomposition. The experiment proved that but one dose – 12.6 kJ/m2 contributed to the deceleration of the anthocyanin decomposition rate, within the range studied. The probable mechanisms that connect ageing and pigment degradation are being discussed. 

  4. LC/PDA/ESI-MS Profiling and Radical Scavenging Activity of Anthocyanins in Various Berries

    Jun-ichiro Nakajima

    2004-01-01

    Full Text Available Anthocyanin extracts of two blueberries, Vaccinium myrtillus (bilberry and Vaccinium ashei (rabbiteye blueberry, and of three other berries, Ribes nigrum (black currant, Aronia melanocarpa (chokeberry, and Sambucus nigra (elderberry, were analyzed by high-performance liquid chromatography coupled with photodiode array detection and electrospray ionization - mass spectrometry (LC/PDA/ESI-MS. Both bilberry and rabbiteye blueberry contained 15 identical anthocyanins with different distribution patterns. Black currant, chokeberry, and elderberry contained 6, 4, and 4 kinds of anthocyanins, respectively. The radical scavenging activities of these berry extracts were analyzed by using 2,2-diphenyl-1-picrylhydrazyl (DPPH. All these extracts showed potent antiradical activities.

  5. Influence of acylation on the adsorption of GLP-2 to hydrophobic surfaces

    Pinholt, Charlotte; Kapp, Sebastian J; Bukrinsky, Jens T; Hostrup, Susanne; Frokjaer, Sven; Norde, Willem; Jorgensen, Lene

    2013-01-01

    Acylation of proteins with a fatty acid chain has proven useful for prolonging the plasma half-lives of proteins. In formulation of acylated protein drugs, knowledge about the effect of acylation with fatty acids on the adsorption behaviour of proteins at interfaces will be valuable. The aim of t...

  6. Two LcbHLH transcription factors interacting with LcMYB1 in regulating late structural genes of anthocyanin biosynthesis in Nicotiana and Litchi chinensis during anthocyanin accumulation

    Biao eLai

    2016-02-01

    Full Text Available Anthocyanin biosynthesis requires the MYB-bHLH-WD40 protein complex to activate the late biosynthetic genes. LcMYB1 was thought to act as key regulator in anthocyanin biosynthesis of litchi. However, basic helix-loop-helix proteins (bHLHs as partners have not been identified yet. The present study describes the functional characterization of three litchi bHLH candidate anthocyanin regulators, LcbHLH1, LcbHLH2 and LcbHLH3. Although these three litchi bHLHs phylogenetically clustered with bHLH proteins involved in anthcoyanin biosynthesis in other plant, only LcbHLH1 and LcbHLH3 were found to localize in the nucleus and physically interact with LcMYB1. The transcription levels of all these bHLHs were not coordinated with anthocyanin accumulation in different tissues and during development. However, when co-infiltrated with LcMYB1, both LcbHLH1 and LcbHLH3 enhanced anthocyanin accumulation in tobacco leaves with LcbHLH3 being the best inducer. Significant accumulation of anthocyanins in leaves transformed with the combination of LcMYB1 and LcbHLH3 were noticed, And this was associated with the up-regulation of two tobacco endogenous bHLH regulators, NtAn1a and NtAn1b, and late structural genes, like NtDFR and NtANS. Significant activity of the ANS promoter was observed in transient expression assays either with LcMYB1-LcbHLH1 or LcMYB1-LcbHLH3, while only minute activity was detected after transformation with only LcMYB1. In contrast, no activity was measured after induction with the combination of LcbHLH2 and LcMYB1. Higher DFR expression was also oberseved in paralleling with higher anthocyanins in co-transformed lines. LcbHLH1 and LcbHLH3 are essential partner of LcMYB1 in regulating the anthocyanin production in tobacco and probably also in litchi. The LcMYB1-LcbHLH complex enhanced anthocyanin accumulation may associate with activating the transcription of DFR and ANS.

  7. A new acylated isoflavone glucoside from Pterocarpus santalinus.

    Krishnaveni, K S; Srinivasa Rao, J V

    2000-09-01

    Phytochemical investigation on the constituents of heartwood of Pterocarpus santalinus resulted in the isolation of a new acylated isoflavone glucoside. The structure of the new compound was elucidated on the basis of spectral studies as 4',5-dihydroxy-7-O-methyl isoflavone 3'-O-D-(3''-E-cinnamoyl)glucoside. PMID:10993243

  8. Enzymatic process for acylation of resveratrol at position 3

    Torres, Pamela; Plou Gasca, Francisco José; Ballesteros Olmo, Antonio

    2008-01-01

    [EN] Enzymatic procedure for the regioselective acylation at position 3 of resveratrol utilising a vinyl ester and specific fungal and bacterial lipases, immobilised, as biocatalyst. The lipases utilised in said procedure come from bacteria or fungi selected from among Alcaligenes, Pseudomonas or Thermomyces.

  9. Medium-chain acyl-CoA dehydrogenase deficiency

    Waddell, Leigh; Wiley, Veronica; Carpenter, Kevin; Bennetts, Bruce; Angel, Lyn; Andresen, Brage S; Wilcken, Bridget

    2006-01-01

    The fatty acid oxidation disorder most commonly identified by tandem mass spectrometry newborn screening is the potentially fatal medium-chain acyl-CoA dehydrogenase deficiency (MCAD). In clinically presenting cases, 80% are homozygous for the common mutation, c.985A > G and 18% heterozygous. We ...

  10. Investigation of the kinetics of acyl group exchange Pt. 6

    Kinetics and mechanism of acyl exchange between 4-nitrophenyl thiolacetate and acetic-1-14C acid or acetic-1-14C anhydride in pyridine and toluene were studied. Comparison of the rate constants and activation parameters to those obtained with 4-nitrophenyl acetate showed a common mechanism for exchange with acetic acid but different pathways for the reaction with acetic anhydride. (author)

  11. Investigation of the kinetics of acyl group exchange Pt. 8

    8-acetoxyquinolines undergo isotopic acyl group exchange with acetic-1-14C acid by the effect of ring nitrogen atom acting as an intramolecular general base catalytic function. Rate constants and activation parameters suggest a reaction mechanism intracomplex in nature. (author)

  12. Investigation of the kinetics of acyl group exchange Pt. 7

    4-nitrophenyl thiol-1-14C acetate exchanges acetyl group with acetyl chloride in nitromethane by the catalytic effect of pyridine. Under the same conditions the ester analogue is unreactive. Kinetic results suggest a common mechanism involving the sulfur atom as reaction site in acyl exchange reactions of thiolester with acetic anhydride and acetyl chloride. (author)

  13. Acyl migration kinetics of vegetable oil 1,2-diacylglycerols

    The acyl migration kinetics of long-chain 1,2-diacylglycerol (1,2-DAG) to form 1,3-diacylglycerol (1,3-DAG) over the temperature range of 25 to 80 degrees Celsius were examined using proton NMR spectroscopy. The 1,2-DAG mole fraction of 0.32 at equilibrium was found to be insensitive to temperature...

  14. Fatty Acyl-CoA Reductase 1 Deficiency

    Charles N Swisher

    2015-01-01

    Full Text Available Investigators from Erlangen, Germany; Calgary, CA; and Kafranbel, Syria, identified mutations in the gene, fatty acyl-CoA reductase 1 (FAR1 deficiency, adding to three other genes involved in plasmalogen biosynthesis, in two families affected by severe intellectual disability, early-onset epilepsy, microcephaly, congenital cataracts, growth retardation, and spasticity.

  15. In vitro production of anthocyanins - A literature review

    The production of secondary metabolites in plant cell cultures may be of interest for obtaining compounds that are difficult to synthesize or isolate from other sources, which is usually associated with high economic value of the substances, but may also be useful to help elucidating the metabolic pathways involved in the synthesis of such compounds. This paper presents a general description of anthocyanins, a group of pigments of great importance to the industry, complemented by referring the scientific papers that have been recently published on their in vitro production. Regarding the latter, a description of the effect of changes in growing conditions, of the addition of precursors, of the use of growth regulators, and of the utilization of elicitors and stressors on the production of these compounds, is done. Finally, this review mentions the use of hairy roots obtained by the use of agrobacterium rhizogenes for the production of these compounds.

  16. Electrochemical and theoretical complexation studies between Zn, Cu and individual anthocyanins in wine samples

    I. Esparza; Salinas, I; Santamaria, C.; Garcia-Mina, J.M. (José María); Fernandez, J.M.

    2004-01-01

    Book of abstracts of Euroanalysis XIII 2004; PS1-280. Identification of the posible interactions between individual anthocyanins and metals was performed in selected samples of must ans wine, collected at different vinification times.

  17. Changes of the Anthocyanins and Antioxidant properties of Concord Grape (Vitis labrusca Pomace After Acid Hydrolysis

    Mustafa Bener

    2016-05-01

    Full Text Available Grape pomace contains high levels of valuable antioxidants such as anthocyanins and phenolic compounds that help prevent chronic diseases such as cardiovascular problems and cancers. In this study, Concord grape pomace was soaked in acidic solutions at different time intervals and pHs in a water bath at 80 oC. Five kinds of anthocyanins were released and identified in the pomace after acid hydrolysis. The releasing rate of anthocyanins and antioxidant activities of the acid hydrolyzed pomace extracts were determined by multitest systems. Different antioxidant assays including total antioxidant capacity (TAC, total phenolic content (TPC and free radical scavenging activity (RSA were used to evaluate the antioxidant properties of the acid hydrolyzed pomace extracts. The change in antioxidant capacity of the pomace extracts during hydrolysis was correlated with total phenolic content and free radical scavenging activity but had little relationship with anthocyanin contents.

  18. Antioxidant capacities and anthocyanin characteristics of the black-red wild berries obtained in Northeast China.

    Feng, Chengyong; Su, Shang; Wang, Lijin; Wu, Jie; Tang, Zhongqiu; Xu, Yanjun; Shu, Qingyan; Wang, Liangsheng

    2016-08-01

    Various edible berries widely accessible in nature in Northeast China are poorly exploited. The compositions and contents of anthocyanins in black (Padus maackii, Padus avium, Lonicera caerulea, and Ribes nigrum) and red (Ribes rubrum, Sambucus williamsii, Rubus idaeus, and Ribes procumbens) wild berries in Northeast China were firstly characterized by HPLC-DAD/ESI-MS(2). Twenty-three anthocyanins were detected and identified. Cyanidin glycosides were dominant in both berries. Six anthocyanins were reported for the first time in P. avium, R. rubrum, and Sambucus. Total anthocyanin content (TAC) ranged from 10mg/100gfreshweight (FW) (R. procumbens) to 1058mg/100gFW (P. maackii) among berries. The TACs and antioxidant activities assessed by DPPH and FRAP assays were much higher in black than in red berries. Black-red berries, especially P. maackii and P. avium, can be used in developing functional foods and in improving breeding programs. PMID:26988488

  19. Developmental effects on phenolic, flavonol, anthocyanin, and carotenoid metabolites and gene expression in potatoes

    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...

  20. Review of Anthocyanins Chemical Studies%花色苷化学研究进展

    郑杰; 丁晨旭; 赵先恩; 索有瑞

    2011-01-01

    Anthocyanins are a kind of widely spread natural colorant,which have raised great interest due to its potent physiological and nutritional effects. Although the great potential of application that anthocyanins represent for food,pharmaceutical and cosmetic industries, their use has been limited because of lack of knowledge about its chemical proper-ties,deficient extraction and identification technology. Currently,many researches are focused on resoling the difficulties. In this paper,the recently advances in anthocyanins research filed are summarised from three parts;anthocyanins chemical chtiractrrizations;extraction and separation technologies;and identification methods.%本文以近期研究报道作为基础从花色苷的化学性质、提取与分离技术、鉴定技术三个方面对花色苷化合物的化学研究进展做一系统综述.

  1. The Immunomodulation Effect of Aronia Extract Lacks Association with Its Antioxidant Anthocyanins

    Mojsoska, Biljana; Xu, Jin

    2013-01-01

    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-alpha and reduced interleukin-10 (IL-10) production by LPS...

  2. Pharmacokinetic Characterization and Bioavailability of Strawberry Anthocyanins Relative to Meal Intake.

    Sandhu, Amandeep K; Huang, Yancui; Xiao, Di; Park, Eunyoung; Edirisinghe, Indika; Burton-Freeman, Britt

    2016-06-22

    Plasma strawberry anthocyanins were characterized in overweight (BMI: 26 ± 2 kg/m(2)) adults (n = 14) on the basis of meal timing. At each visit, subjects ingested three study drinks: two control and one strawberry drink. A strawberry drink was given at either 2 h before the breakfast meal (BM), with the meal (WM), or 2 h after the meal (AM), and control drinks were given at the alternative time points. Plasma anthocyanins and their metabolic conjugates were assessed hourly for 10 h using a triple-quadrupole liquid chromatography mass spectrometer. Maximum concentrations (Cmax), area under the curve (AUC), and bioavailability of pelargonidin-based anthocyanins determined from the main conjugated metabolite (pelargonidin glucuronide) were greater when a strawberry drink was consumed 2 h before the meal (BM) compared to consumption WM or AM (p strawberry consumption relative to a meal impacts anthocyanin pharmacokinetic variables. PMID:27255121

  3. Impact of Frozen Storage on the Anthocyanin and Polyphenol Contents of American Elderberry Fruit Juice.

    Johnson, Mitch C; Thomas, Andrew L; Greenlief, C Michael

    2015-06-17

    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. PMID:26028422

  4. Impact of Frozen Storage on the Anthocyanin and Polyphenol Content of American Elderberry Fruit Juice

    Johnson, Mitch C.; Thomas, Andrew L.; Greenlief, C. Michael

    2015-01-01

    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

  5. Harvest date affects aronia juice polyphenols, sugars, and antioxidant activity, but not anthocyanin stability.

    Bolling, Bradley W; Taheri, Rod; Pei, Ruisong; Kranz, Sarah; Yu, Mo; Durocher, Shelley N; Brand, Mark H

    2015-11-15

    The goal of this work was to characterize how the date of harvest of 'Viking' aronia berry impacts juice pigmentation, sugars, and antioxidant activity. Aronia juice anthocyanins doubled at the fifth week of the harvest, and then decreased. Juice hydroxycinnamic acids decreased 33% from the first week, while proanthocyanidins increased 64%. Juice fructose and glucose plateaued at the fourth week, but sorbitol increased 40% to the seventh harvest week. Aronia juice pigment density increased due to anthocyanin concentration, and polyphenol copigmentation did not significantly affect juice pigmentation. Anthocyanin stability at pH 4.5 was similar between weeks. However, addition of quercetin, sorbitol, and chlorogenic acid to aronia anthocyanins inhibited pH-induced loss of color. Sorbitol and citric acid may be partially responsible for weekly variation in antioxidant activity, as addition of these agents inhibited DPPH scavenging 13-30%. Thus, aronia polyphenol and non-polyphenol components contribute to its colorant and antioxidant functionality. PMID:25977015

  6. Specificity of Acyl-Homoserine Lactone Synthases Examined by Mass Spectrometry

    Gould, Ty A.; Herman, Jake; Krank, Jessica; Robert C. Murphy; Mair E A Churchill

    2006-01-01

    Many gram-negative bacteria produce a specific set of N-acyl-l-homoserine-lactone (AHL) signaling molecules for the purpose of quorum sensing, which is a means of regulating coordinated gene expression in a cell-density-dependent manner. AHLs are produced from acylated acyl-carrier protein (acyl-ACP) and S-adenosyl-l-methionine by the AHL synthase enzyme. The appearance of specific AHLs is due in large part to the intrinsic specificity of the enzyme for subsets of acyl-ACP substrates. Structu...

  7. Fatty acyl-CoA reductases of birds

    Hellenbrand Janine

    2011-12-01

    Full Text Available Abstract Background Birds clean and lubricate their feathers with waxes that are produced in the uropygial gland, a holocrine gland located on their back above the tail. The type and the composition of the secreted wax esters are dependent on the bird species, for instance the wax ester secretion of goose contains branched-chain fatty acids and unbranched fatty alcohols, whereas that of barn owl contains fatty acids and alcohols both of which are branched. Alcohol-forming fatty acyl-CoA reductases (FAR catalyze the reduction of activated acyl groups to fatty alcohols that can be esterified with acyl-CoA thioesters forming wax esters. Results cDNA sequences encoding fatty acyl-CoA reductases were cloned from the uropygial glands of barn owl (Tyto alba, domestic chicken (Gallus gallus domesticus and domestic goose (Anser anser domesticus. Heterologous expression in Saccharomyces cerevisiae showed that they encode membrane associated enzymes which catalyze a NADPH dependent reduction of acyl-CoA thioesters to fatty alcohols. By feeding studies of transgenic yeast cultures and in vitro enzyme assays with membrane fractions of transgenic yeast cells two groups of isozymes with different properties were identified, termed FAR1 and FAR2. The FAR1 group mainly synthesized 1-hexadecanol and accepted substrates in the range between 14 and 18 carbon atoms, whereas the FAR2 group preferred stearoyl-CoA and accepted substrates between 16 and 20 carbon atoms. Expression studies with tissues of domestic chicken indicated that FAR transcripts were not restricted to the uropygial gland. Conclusion The data of our study suggest that the identified and characterized avian FAR isozymes, FAR1 and FAR2, can be involved in wax ester biosynthesis and in other pathways like ether lipid synthesis.

  8. Molecular evolution of anthocyanin pigmentation genes following losses of flower color

    Ho, Winnie W.; Smith, Stacey D.

    2016-01-01

    Background Phenotypic transitions, such as trait gain or loss, are predicted to carry evolutionary consequences for the genes that control their development. For example, trait losses can result in molecular decay of the pathways underlying the trait. Focusing on the Iochrominae clade (Solanaceae), we examine how repeated losses of floral anthocyanin pigmentation associated with flower color transitions have affected the molecular evolution of three anthocyanin pathway genes (Chi, F3h, and Df...

  9. Caffeoylquinic Acids Generated In Vitro in a High-Anthocyanin-Accumulating Sweet potato Cell Line

    Izabela Konczak; Shigenori Okuno; Makoto Yoshimoto; Osamu Yamakawa

    2004-01-01

    Accumulation of phenolic compounds has been monitored in a suspension culture of anthocyanin-accumulating sweet potato cell line grown under the conditions of modified Murashige and Skoog high-anthocyanin production medium (APM) over a period of 24 days. Tissue samples extracted with 15% acetic acid were analysed using HPLC at a detection wavelength of 326 nm. Among others, the following derivatives of caffeoylquinic acids were detected: 4,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 3...

  10. A candidate-gene association study for berry colour and anthocyanin content in Vitis vinifera L.

    Silvana Cardoso

    Full Text Available 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 MYC(B 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, MYC(B, UFGT, MRP, DFR, LDOX, CHI and GST. Pulp colour was associated with a similar group of 11 genes (MYB11, MYBCC, MYC(B, MYC(A, UFGT, MRP, GST, DFR, LDOX, CHI and CHS(A. Statistical interactions were observed between SNPs within the transcription factors MYB11, MYBCC and MYC(B. SNPs within LDOX interacted with MYB11 and MYC(B, 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.

  11. In Vitro and in Vivo Anti-Diabetic Effects of Anthocyanins from Maqui Berry (Aristotelia chilensis)

    Rojo, Leonel E.; Ribnicky, David; Logendra, Sithes; Poulev, Alex; Rojas-Silva, Patricio; Kuhn, Peter; Dorn, Ruth; Grace, Mary H; Lila, Mary Ann; Raskin, Ilya

    2011-01-01

    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 a...

  12. Anthocyanin Characterization of Pilot Plant Water Extracts of Delonix regia Flowers

    Gaydou, Emile M.; Georges Agbo N’zi; Augustin Adima; Paul Lozano; Emmanuelle Meudec; Lozano, Yves F.; Felix Adje

    2008-01-01

    Following the development of new applications of pilot plant scale extraction and formulation processes for natural active bioproducts obtained from various under-utilized tropical plants and herbs, we have manufactured water-extracts from Delonix regia flowers, grown in Ivory Coast. These extracts, which contain polyphenols, are traditionally home made and used as healthy bioproducts. They are reddish-coloured due to the presence of anthocyanins. The three major anthocyanins in these extract...

  13. Two glycosyltransferases involved in anthocyanin modification delineated by transcriptome independent component analysis in Arabidopsis thaliana

    Yonekura-Sakakibara, Keiko; Fukushima, Atsushi; Nakabayashi, Ryo; Hanada, Kousuke; Matsuda, Fumio; Sugawara, Satoko; Inoue, Eri; Kuromori, Takashi; ITO, Takuya; Shinozaki, Kazuo; Wangwattana, Bunyapa; Yamazaki, Mami; Saito, Kazuki

    2011-01-01

    To identify candidate genes involved in Arabidopsis flavonoid biosynthesis, we applied transcriptome coexpression analysis and independent component analyses with 1388 microarray data from publicly available databases. Two glycosyltransferases, UGT79B1 and UGT84A2 were found to cluster with anthocyanin biosynthetic genes. Anthocyanin was drastically reduced in ugt79b1 knockout mutants. Recombinant UGT79B1 protein converted cyanidin 3-O-glucoside to cyanidin 3-O-xylosyl(1→2)glucoside. UGT79B1 ...

  14. Anthocyanin absorption and metabolism by human intestinal Caco-2 cells: a review

    Senem Kamiloglu; Esra Capanoglu; Charlotte Grootaert; John Van Camp

    2015-01-01

    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...

  15. An Intracellular Laccase Is Responsible for Epicatechin-Mediated Anthocyanin Degradation in Litchi Fruit Pericarp.

    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

    2015-12-01

    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. PMID:26514808

  16. ANTHOCYANIN PIGMENTATION IN TRITICUM AESTIVUM L.: GENETIC BASIS AND ROLE UNDER ABIOTIC STRESS CONDITIONS

    Tereshchenko O.Yu.; E.I. Gordeeva; V.S. Arbuzova; E.K. Khlestkina

    2012-01-01

    Anthocyanins are secondary metabolites of plants. They have a wide range of biological activity such as antioxidant, photoprotection, osmoregulation, heavy metal ions chelation, antimicrobial and antifungal activities, which help plants to survive under different stress conditions. Bread wheat (T. aestivum L.) can have purple pigmentation provided by anthocyanin compounds in different organs, such as grain pericarp, coleoptile, culm, leaf blades, leaf sheaths, glumes and anthers. However, the...

  17. Relationship Between Anthocyanin Biosynthesis and Related Enzymes Activity in Pyrus pyrifolia Mantianhong and Its Bud Sports Aoguan

    FENG Shou-qian; CHEN Xue-sen; ZHANG Chun-yu; LIU Xiao-jing; LIU Zun-chun; WANG Hai-bo; WANG Yan-ling; ZHOU Chao-hua

    2008-01-01

    The aim of this article is to study the relationship between biosynthesis of anthocyanin and activities of phenylalanine ammonia lyase (PAL), chalcone ismoerase (CHI) enzymes in Pyrus pyrifolia. Changes in the level of anthocyanin and the activities of enzymes of anthocyanin biosynthesis including PAL, CH1 were studied in the pericarp of Pyrus pyrifolia Aoguan and Mantianhong during the period of pigment formation. Bagging treatment was also carried out to manipulate the synthesis of anthocyanin and the activities of related enzymes during the period of pigment formation. The results demonstrated that the level of anthocyanin of Aoguan was higher than that of Mantianhong. However, the content of anthocyanins has the similar changing trend in Aoguan and Mantianhong, highest anthocyanin concentrations of two varieties appeared in immature fruit and faded toward harvest. Meanwhile, similar changing trends of activities of PAL and CHI were also observed in both varieties. Aoguan has a lower activity of PAL than Mantianhong, whereas activity of CHI in Aoguan was higher than that in Mantianhong. Activity of PAL decreased during the period of pigment formation and was apparently not limiting to color development, whereas CHI activity increased at the same period and was closely related to the synthesis of anthocyanin. The results of bagging treatment showed that bagging treatment inhibited the activity of CHI, as well as the synthesis of anthocyanin, whereas debagging enhanced both the activity of CHI and synthesis of anthocyanin. The activity of CHI in debagging Aoguan pericarp was higher than the untreated Aoguan. However, effect of bagging treatment toward PAL activity was not obvious. Anthocyanin of bagging treated Aoguan decreased toward harvest. The content of anthocyanin of Pyrus pyrifolia increased at the beginning of fruit coloration period and decreased toward fruit harvest. Activity of PAL was apparently not limiting to color development, whereas CHI activity

  18. Methylation mediated by an anthocyanin, O-methyltransferase, is involved in purple flower coloration in Paeonia.

    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

    2015-11-01

    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

  19. Correlation Between Antioxidation and the Content of Total Phenolics and Anthocyanin in Black Soybean Accessions

    XU Jin-rui; ZHANG Ming-wei; LIU Xing-hua; LIU Zhang-xiong; ZHANG Rui-fen; SUN Ling; QIU Li-juan

    2007-01-01

    The objective of this study was to investigate the correlations between antioxidations and the contents of the total phenolics and anthocyanin in 127 accessions of black soybean. A T-test, a fast clustering procedure, and a correlation coefficient analysis were used for experimentation. The variation ranges of the total antioxidant capacity (TAC), the total phenolics, and anthocyanin contents in 127 black soybean accessions were 0.44-3.56, 7.05-74.82, and 0.22-1.87mg g-1, respectively, displaying significant genotype differences. The major differences in TAC, the total phenolics,and the anthocyanin contents existed among various types of accessions from geographical regions. The differences between the accessions from black and yellow soybeans, spring and autumn, summer and autumn, Dongbeichun and Nanfangchun, Dongbeichun and Nanfangxia, Beifangchun and Nanfangchun, and Beifangchun and Nanfangxia were significant at 0.01 or 0.05 levels, respectively. The general tendency was that the TAC, the total phenolics, and the anthocyanin contents of Beifangchun accessions were higher than that of Dongbeichun ones, while that of Nanfangchun accessions were the worst. 127 black soybean accessions could be clustered into 6 clusters, which consisted of 3, 24,20, 31, 37, and 12 accessions, respectively. The most significant (P < 0.01) correlations existed respectively between the TAC and the total phenolics content, and the TAC and the anthocyanin content of black soybean. The results showed that the total phenolics and anthocyanin in black soybean seed coat were the important antioxidation substances.

  20. Antiproliferative and Antioxidant Properties of Anthocyanin Rich Extracts from Blueberry and Blackcurrant Juice

    Zoriţa Diaconeasa

    2015-01-01

    Full Text Available 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.

  1. Stability of Anthocyanins from Rubus glaucus and Solanum betaceum as affected by Temperature and Water Activity

    Garzon Monroy Gloria Astrid

    2009-12-01

    Full Text Available The stability of sprayed-dried microencapsulated anthocyanins from Andes berry (Rubus glaucus and Tamarillo (Solanum betaceum, as affected by storage time, water activity (Aw and temperature was compared. The fruits were osmotically dehydrated with ethanol and the anthocyanin extract was microencapsulated with maltodextrin DE 20 by spray drying. Half life of the anthocyanins; changes in color, total phenolics, and antioxidant activity of the powders, were analyzed during storage at two different temperatures (25 °C and 40 °C and two Aw levels (0.20 and 0.35. A decrease in monomeric anthocyanin was observed in both samples. The half life of the Andes berry pigments ranged between 11 and 32 days while the half life of the tamarillo pigments ranged between 9 and 21 days. A darkening effect occurred in both samples as a result of storage time.  The antioxidant activity decreased while the phenolic content increased with time. Antioxidant activity of Andes berry samples was highly correlated with anthocyanin content and total phenolic content while the antioxidant activity of tamarillo samples was highly correlated with total phenolic content. These results would be useful in developing applications for spray-dried anthocyanin as powdered food-grade colorants.

  2. Protective Effect of Anthocyanins from Lingonberry on Radiation-induced Damages

    Shuang-Qi Tian

    2012-12-01

    Full Text Available 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.

  3. Stabilization of natural colors and nutraceuticals: Inhibition of anthocyanin degradation in model beverages using polyphenols.

    Chung, Cheryl; Rojanasasithara, Thananunt; Mutilangi, William; McClements, David Julian

    2016-12-01

    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. PMID:27374573

  4. Enhancement of colour stability of anthocyanins in model beverages by gum arabic addition.

    Chung, Cheryl; Rojanasasithara, Thananunt; Mutilangi, William; McClements, David Julian

    2016-06-15

    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. PMID:26868542

  5. Incorporating graphene in anthocyanin-based dye-sensitized solar cells

    The use of natural dyes as sensitizer for dye-sensitized solar cells (DSSC) offers significant advantages such as attainability and cheaper production cost. However, its low power conversion efficiency (PCE) impedes its wide utilization. In this study, enhancement in efficiency of anthocyanin-based dye sensitized solar cells through the incorporation of graphene was studied. Graphene is a two-dimensional sheet of sp”2-hyridized carbon known for its extraordinary mechanical, thermal and electrical properties. This remarkable material was incorporated in the TiO2 photoanode or with anthocyanin dye dispersion. Current-voltage (IV) and electrochemical impedance spectroscopy (EIS) measurements were carried out to characterize the anthocyanin-based DSSC. Addition of graphene ration into TiO2 as a photoanode composite and/or in anthocyanin extracts (anthocyanin: graphene dispersion) gave the same positive effect, an increase in PCE from 0.185% without graphene to as high as 0.516% with combined graphene doping of the TiO2 and using an anthocyanin: graphene dye dispersion. Furthermore, a 30% increase in fill factor was obtained for DSSCs in the presence of graphene. EIS data showed a favourable decrease in charge transfer resistance in the TiO2 layer as graphene is added to the DSSC, with increased magnitude of the short-circuit current (Jsc). This is explained by graphene providing added conducting pathways for the photo-generated electrons. (author)

  6. Functional characterization of Dihydroflavonol-4-reductase in anthocyanin biosynthesis of purple sweet potato underlies the direct evidence of anthocyanins function against abiotic stresses.

    Hongxia Wang

    Full Text Available 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.

  7. The food matrix affects the anthocyanin profile of fortified egg and dairy matrices during processing and in vitro digestion.

    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

    2017-01-01

    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. PMID:27507502

  8. HPLC/1H NMR spectroscopic studies of the reactive alpha-1-O-acyl isomer formed during acyl migration of S-naproxen beta-1-O-acyl glucuronide.

    Corcoran, O; Mortensen, R W; Hansen, S H; Troke, J; Nicholson, J K

    2001-10-01

    A widely held view in drug metabolism and pharmacokinetic studies is that the initial 1-isomer to 2-isomer step in the intramolecular acyl migration of drug ester glucuronides is irreversible, and that alpha-1-O-acyl isomers do not occur under physiological conditions. We investigated this hypothesis using high-performance liquid chromatography directly coupled to proton nuclear magnetic resonance spectroscopy (HPLC/1H NMR) and mass spectrometry (LC/MS) to probe the migration reactions of S-naproxen beta-1-O-acyl glucuronide, in phosphate buffer at pH 7.4, 37 degrees C. We report the first direct observation of the alpha-1-O-acyl isomer of a drug ester glucuronide (S-naproxen) formed in a biosystem via the facile acyl migration of the corresponding pure beta-1-O-acyl glucuronide. The unequivocal identification of the reactive product was achieved using stopped-flow one-dimensional HPLC/1H NMR and two-dimensional 1H-1H total correlation spectroscopy (1H-1H TOCSY). Parallel LC/ion-trap mass spectrometry yielded the confirmatory glucuronide masses. Moreover, "dynamic" stopped-flow HPLC/1H NMR experiments revealed transacylation of the isolated alpha-1-O-acyl isomer to a mixture of alpha/beta-2-O-acyl isomers; the reverse reaction from the isolated alpha/beta-2-O-acyl isomers to the alpha-1-O-acyl isomer was also clearly demonstrated. This application of "dynamic" stopped-flow HPLC/1H NMR allows key kinetic data to be obtained on a reactive metabolite that would otherwise be difficult to follow by conventional HPLC and NMR methods where sample preparation and off-line separations are necessary. These data challenge the widely held view that the alpha-1-O-acyl isomers of drug ester glucuronides do not occur under physiological conditions. Furthermore, the similar formation of alpha-1-O-acyl isomers from zomepirac and diflunisal beta-1-O-acyl glucuronides has recently been confirmed (Corcoran et al., unpublished results). Such reactions are also likely to be widespread

  9. Overexpressing CAPRICE and GLABRA3 did not change the anthocyanin content of tomato (solanum lycopersicum) fruit peel

    Wada, Takuji; Onishi, Mio; Kunihiro, Asuka; Tominaga-Wada, Rumi

    2015-01-01

    In Arabidopsis thaliana, the R3-type MYB transcription factor CAPRICE (CPC) and bHLH transcription factor GLABRA3 (GL3) cooperatively regulate epidermal cell differentiation. CPC and GL3 are involved in root-hair differentiation, trichome initiation and anthocyanin biosynthesis in Arabidopsis epidermal cells. Previously, we showed that CPC and GL3 also influence anthocyanin accumulation in tomato. Introduction of 35S::CPC into tomato significantly inhibits anthocyanin accumulation in cotyledo...

  10. Gene regulation of anthocyanin biosynthesis in two blood-flesh peach (Prunus persica (L.) Batsch) cultivars during fruit development* #

    Jiao, Yun; Ma, Rui-juan; Shen, Zhi-Jun; Yan, Juan; Yu, Ming-liang

    2014-01-01

    The blood-flesh peach has become popular in China due to its attractive anthocyanin-induced pigmentation and antioxidant properties. In this study, we investigated the molecular mechanisms underlying anthocyanin accumulation by examining the expression of nine genes of the anthocyanin biosynthesis pathway found in the peach mesocarp. Expression was measured at six developmental stages in fruit of two blood-flesh and one white-flesh peach cultivars, using quantitative reverse transcription pol...

  11. Gibberellins negatively regulate low temperature-induced anthocyanin accumulation in a HY5/HYH-dependent manner

    Zhang, Yongqiang; Liu, Zhongjuan; Liu, Rongzhi; Hao, Hualing; Bi, Yurong

    2011-01-01

    Low temperature could significantly induce anthocyanin accumulation in the presence of light. Recently, two bZIP transcription factors LONG HYPOCOTYL 5 (HY5) and HOMOLOG OF HY5 (HYH) were identified to play an important role in the process of low temperature-induced anthocyanin accumulation. However, the mechanism by which HY5/HYH regulates anthocyanin accumulation under low temperature still remains unclear. Here, we found that the gibberellins (GAs) could decrease but PAC (endogenous GAs bi...

  12. A Novel bHLH Transcription Factor Involved in Regulating Anthocyanin Biosynthesis in Chrysanthemums (Chrysanthemum morifolium Ramat.)

    Li-li Xiang; Xiao-fen Liu; Xue Li; Xue-ren Yin; Donald Grierson; Fang Li; Kun-song Chen

    2015-01-01

    Chrysanthemums (Chrysanthemum morifolium Ramat.) exhibit a variety of flower colors due to their differing abilities to accumulate anthocyanins. One MYB member, CmMYB6, has been verified as a transcription regulator of chrysanthemum genes involved in anthocyanin biosynthesis; however, the co-regulators for CmMYB6 remain unclear in chrysanthemum. Here, the expression pattern of CmbHLH2, which is clustered in the IIIf bHLH subgroup, was shown to be positively correlated with the anthocyanin con...

  13. Sunlight-stimulated phenylalanine ammonia-lyase (PAL) activity and anthocyanin accumulation in exocarp of ‘Mahajanaka’ mango

    Kobkiat Saengnil

    2011-01-01

    The activity of phenylalanine ammonia-lyase (PAL) required for anthocyanin synthesis was stimulated by sunlight exposure resulting in the development of red colour in ‘Mahajanaka’ mango exocarp, which occurred only on the sunlight-exposed side of the fruit. The accumulation of anthocyanin was concurrent with the increase in PAL activity in the mature stage of the fruit. The exposed side of the fruit had higher PAL activity, endogenous sugar content, and anthocyanin accumulation than the unexp...

  14. Differential Expression of Anthocyanin Biosynthetic Genes and Transcription Factor PcMYB10 in Pears (Pyrus communis L.)

    Li LI; Ban, Zhao-Jun; Li, Xi-Hong; Wu, Mao-Yu; Wang, Ai-Li; Jiang, Yu-Qian; Jiang, Yun-Hong

    2012-01-01

    Anthocyanin biosynthesis in various plants is affected by environmental conditions and controlled by the transcription level of the corresponding genes. In pears (Pyrus communis cv. ‘Wujiuxiang’), anthocyanin biosynthesis is significantly induced during low temperature storage compared with that at room temperature. We further examined the transcriptional levels of anthocyanin biosynthetic genes in ‘Wujiuxiang’ pears during developmental ripening and temperature-induced storage. The expressio...

  15. Control of anthocyanin biosynthesis pathway gene expression by eutypine, a toxin from Eutypa lata, in grape cell tissue cultures

    Afifi, Maha; El-Kereamy, Ashraf; Legrand, Valérie; Chervin, Christian; Monje, Marie-Carmen; Nepveu, Françoise; Roustan, Jean-Paul

    2003-01-01

    Eutypine, 4-hydroxy-3-(3-methyl-3-butene-1-ynyl) benzaldehyde, is a toxin produced by Eutypa lata, the causal agent of Eutypa dieback in grapevine. The effect of the toxin on anthocyanin synthesis has been investigated in Vitis vinifera cv. Gamay cell cultures. At concentrations higher than 200 μmol/L, eutypine reduced anthocyanin accumulation in cells. The reduction in anthocyanin accumulation was proportional to the eutypine concentrations and HPLC analysis showed that eutypine ...

  16. Decreasing pH Results in a Reduction of Anthocyanin Coprecipitation during Cold Stabilization of Purple Grape Juice

    Manns, David C.; Passaporn Siricururatana; Olga I. Padilla-Zakour; Sacks, Gavin L.

    2015-01-01

    Anthocyanin pigments in grape juice can coprecipitate with potassium bitartrate (KHT) crystals during cold stabilization, but factors that reduce these adsorptive losses are not well understood. We hypothesized that coprecipitation on a % w/w basis should be decreased at lower pH. In initial experiments, model juice solutions containing an anthocyanin monoglucoside extract and varying pH values were subjected to cold-storage to induce KHT crystallization, and anthocyanins in the resulting pre...

  17. The effect of sugars in relation to methyl jasmonate on anthocyanin formation in the roots of Kalanchoe blossfeldiana (Poelln.)

    Justyna Góraj-Koniarska; Marian Saniewski

    2015-01-01

    This study investigated the effects of different sugars (sucrose, fructose, glucose) and sugar alcohols (mannitol, sorbitol) applied alone and in solution with methyl jasmonate (JA-Me) on the anthocyanin content in the roots of Kalanchoe blossfeldiana. None of the sugars used individually in the experiment affected anthocyanin accumulation in the roots of intact plants. The anthocyanin level was similar to that in the control. Sucrose at concentrations of 0.5% and 3.0%, and glucose at a conce...

  18. Optimization of Extraction Parameters by Using Response Surface Methodology, Purification, and Identification of Anthocyanin Pigments in Melastoma malabathricum Fruit

    Nordiyanah Anuar; Ahmad Faris Mohd Adnan; Naziz Saat; Norkasmani Aziz; Rosna Mat Taha

    2013-01-01

    Anthocyanins not just have various benefits in food industry but also have been used as natural colourants in cosmetic, coating products and as potential natural photosensitizers in solar cell. Thus, the main purpose of this study was to obtain information on the maximum yield of anthocyanin that can be recovered from Melastoma malabathricum fruit. Factors such as extraction temperature, extraction time, and solid to liquid ratio were identified to be significantly affecting anthocyanin extra...

  19. The effect of solvents on the stabilities (color and Fe) of anthocyanin isolated from the red-color-melinjo peels

    Tarmizi, Ermiziar; Lalasari, Latifa Hanum; Saragih, Raskita

    2015-12-01

    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.

  20. VIGS approach reveals the modulation of anthocyanin biosynthetic genes by CaMYB in chili pepper leaves

    Zhang, Zhen; Li, Da-Wei; Jin, Jing-Hao; Yin, Yan-Xu; Zhang, Huai-Xia; Chai, Wei-Guo; Gong, Zhen-Hui

    2015-01-01

    The purple coloration of pepper leaves arises from the accumulation of anthocyanin. Three regulatory and 12 structural genes have been characterized for their involvement in the anthocyanin biosynthesis. Examination of the abundance of these genes in leaves showed that the majority of them differed between anthocyanin pigmented line Z1 and non-pigmented line A3. Silencing of the R2R3-MYB transcription factor CaMYB in pepper leaves of Z1 resulted in the loss of anthocyanin accumulation. Moreov...

  1. The effect of solvents on the stabilities (color and Fe) of anthocyanin isolated from the red-color-melinjo peels

    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

  2. The effect of solvents on the stabilities (color and Fe) of anthocyanin isolated from the red-color-melinjo peels

    Tarmizi, Ermiziar, E-mail: uph-ermi@yahoo.com, E-mail: ermitarmizi@gmail.com; Saragih, Raskita, E-mail: raskitasaragih@yahoo.com [Indonesia Institute of Technology (ITI), Raya PuspiptekSerpong, Tangerang Banten 15320 (Indonesia); Lalasari, Latifa Hanum, E-mail: ifa-sari@yahoo.com, E-mail: lati003@lipi.go.id [Research Centre for Metallurgy and Material, Indonesian Institute of Sciences (LIPI), KawasanPuspiptekSerpong, Tangerang Selatan 15314 (Indonesia)

    2015-12-29

    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.

  3. DNA Damage Protecting Activity and Free Radical Scavenging Activity of Anthocyanins from Red Sorghum (Sorghum bicolor) Bran

    P. Suganya Devi; M. Saravana Kumar; S. Mohan Das

    2012-01-01

    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 flavon...

  4. Vectorial acylation in Saccharomyces cerevisiae. Fat1p and fatty acyl-CoA synthetase are interacting components of a fatty acid import complex

    Zou, Zhiying; Tong, Fumin; Færgeman, Nils J.;

    2003-01-01

    In Saccharomyces cerevisiae Fat1p and fatty acyl-CoA synthetase (FACS) are hypothesized to couple import and activation of exogenous fatty acids by a process called vectorial acylation. Molecular genetic and biochemical studies were used to define further the functional and physical interactions ...

  5. Lipase-catalyzed biodiesel synthesis with different acyl acceptors

    Ognjanović Nevena D.

    2008-01-01

    Full Text Available Biodiesel is an alternative fuel for diesel engine that is environmentally acceptable. Conventionally, biodiesel is produced by transesterification of triglycerides and short alcohols in the presence of an acid or an alkaline catalyst. There are several problems associated with this kind of production that can be resolved by using lipase as the biocatalyst. The aim of the present work was to investigate novel acyl acceptors for biodiesel production. 2-Propanol and n-butanol have a less negative effect on lipase stability, and they also improve low temperature properties of the fuel. However, excess alcohol leads to inactivation of the enzyme, and glycerol, a major byproduct, can block the immobilized enzyme, resulting in low enzymatic activity. This problem was solved by using methyl acetate as acyl acceptor. Triacetylglycerol is produced instead of glycerol, and it has no negative effect on the activity of the lipase.

  6. Site-Selective Acylations with Tailor-Made Catalysts.

    Huber, Florian; Kirsch, Stefan F

    2016-04-18

    The acylation of alcohols catalyzed by N,N-dimethylamino pyridine (DMAP) is, despite its widespread use, sometimes confronted with substrate-specific problems: For example, target compounds with multiple hydroxy groups may show insufficient selectivity for one hydroxyl, and the resulting product mixtures are hardly separable. Here we describe a concept that aims at tailor-made catalysts for the site-specific acylation. To this end, we introduce a catalyst library where each entry is constructed by connecting a variable and readily tuned peptide scaffold with a catalytically active unit based on DMAP. For selected examples, we demonstrate how library screening leads to the identification of optimized catalysts, and the substrates of interest can be converted with a markedly enhanced site-selectivity compared with only DMAP. Furthermore, substrate-optimized catalysts of this type can be used to selectively convert "their" substrate in the presence of structurally similar compounds, an important requisite for reactions with mixtures of substances. PMID:26970553

  7. Synthesis and characterization of new amino acyl-4-thiazolidones

    Ana Cristina Lima Leite

    2007-04-01

    Full Text Available A series of heterocyclic compounds with a 4-thiazolidone nucleus and amino acyl moiety were synthesized by protection reaction of thiosemicarbazide using the symmetrical anhydride (Boc2O and cyclization with chloroacetic acid under mild conditions. Trifluoroacetic acid was used to obtain 4-thiazolidone and the alpha-amino acid condensation reactions were carried out using strategies for peptide synthesis. The characterization of this new class of compounds was performed using IR and ¹H-NMR spectroscopy.

  8. Investigation of the kinetics of acyl group exchange Pt. 5

    Kinetics and catalysis mechanism of acyl exchange between 4-nitro-phenyl acetate and acetic-1-C-14 acid catalyzed by pyridine bases (pyridine, 3-methyl, 4-methyl, 4-terc.butyl, 3,4-dimethyl, 3,5-dimethyl pyridine) were studied in several aprotic solvents. Logarithms of rate constants were correlated with pKsub(a)'s of bases in water and in acetonitrile. Bronsted coefficients indicate a general base catalytic action by the above bases. (author)

  9. Investigation of the kinetics of acyl group exchange Part 4

    Kinetics and mechanism of acyl exchange between substituted phenyl acetates and acetic-1-14C anhydride in pyridine solvent were investigated. The excellent Hammett correlation with sigma-sup(*) and Σsigma-sup(*) values for the exchange reaction of 2-nitro- and 2,6-dinitrophenyl acetates, respectively, as well as the similar values for ΔSsup(*) demonstrate the absence of any detectable ortho effect. (author)

  10. Estimating contribution of anthocyanin pigments to osmotic adjustment during winter leaf reddening.

    Hughes, Nicole M; Carpenter, Kaylyn L; Cannon, Jonathan G

    2013-01-15

    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

  11. Scientific Opinion on the re-evaluation of anthocyanins (E 163 as a food additive

    EFSA Panel on Food Additives and Nutrient Sources added to Food (ANS

    2013-04-01

    Full Text Available Following a request from the European Commission to the European Food Safety Authority (EFSA, the Scientific Panel on Food Additives and Nutrient Sources added to Food (ANS was asked to provide a scientific opinion re-evaluating the safety of anthocyanins (E 163. The Panel concluded that the currently available toxicological database was inadequate to establish a numerical ADI for anthocyanins. For anthocyanins extracted from edible fruits and vegetables by aqueous processes, changes in composition would not be expected. The Panel concluded that provided exposure from use as a food additive was comparable to that from the diet the underlying conclusion in the 1975 SCF opinion that such food additives derived from natural sources would still apply. The majority of data are on aqueous grape skin extract (GSKE and blackcurrant extracts and the Panel considers that exposures estimated from current uses and use levels these extracts are unlikely to be of safety concern. The Panel recommends that the specifications for E 163 should be modified to reflect this conclusion. For anthocyanins extracted from other sources and/or using non-aqueous extraction methods the absence of characterisation does not allow verification that this conclusion in the 1975 SCF opinion could be applied. The Panel noted that for some extracts it had proven possible to assess a group based on toxicological and compositional data on representative samples across the range of extracts. The Panel concluded that refined exposure estimates of anthocyanins used as a food additive were higher than dietary intakes and that these did not include intakes from colouring foods. Therefore the Panel would recommend that appropriate characterisation and toxicological data should be required to permit a further re-evaluation of anthocyanins including comparative data on anthocyanins (E 163 produced by aqueous extraction.

  12. Stabilisation of strawberry (Fragaria x ananassa Duch.) anthocyanins by different pectins.

    Buchweitz, M; Speth, M; Kammerer, D R; Carle, R

    2013-12-01

    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. PMID:23871051

  13. The ɛ-Amino Group of Protein Lysine Residues Is Highly Susceptible to Nonenzymatic Acylation by Several Physiological Acyl-CoA Thioesters.

    Simic, Zeljko; Weiwad, Matthias; Schierhorn, Angelika; Steegborn, Clemens; Schutkowski, Mike

    2015-11-01

    Mitochondrial enzymes implicated in the pathophysiology of diabetes, cancer, and metabolic syndrome are highly regulated by acetylation. However, mitochondrial acetyltransferases have not been identified. Here, we show that acetylation and also other acylations are spontaneous processes that depend on pH value, acyl-CoA concentration and the chemical nature of the acyl residue. In the case of a peptide derived from carbamoyl phosphate synthetase 1, the rates of succinylation and glutarylation were up to 150 times than for acetylation. These results were confirmed by using the protein substrate cyclophilin A (CypA). Deacylation experiments revealed that SIRT3 exhibits deacetylase activity but is not able to remove any of the succinyl groups from CypA, whereas SIRT5 is an effective protein desuccinylase. Thus, the acylation landscape on lysine residues might largely depend on the enzymatic activity of specific sirtuins, and the availability and reactivity of acyl-CoA compounds. PMID:26382620

  14. Synthesis and biological activities of turkesterone 11?-acyl derivatives

    Laurence Dinan

    2003-02-01

    Full Text Available Turkesterone is a phytoecdysteroid possessing an 11alpha-hydroxyl group. It is an analogue of the insect steroid hormone 20-hydroxyecdysone. Previous ecdysteroid QSAR and molecular modelling studies predicted that the cavity of the ligand-binding domain of the ecdysteroid receptor would possess space in the vicinity of C-11/C-12 of the ecdysteroid. We report the regioselective synthesis of a series of turkesterone 11alpha-acyl derivatives in order to explore this possibility. The structures of the analogues have been unambiguously determined by spectroscopic means (NMR and low-resolution mass spectrometry. Purity was verified by HPLC. Biological activities have been determined in Drosophila melanogaster BII cell-based bioassay for ecdysteroid agonists and in an in vitro radioligand-displacement assay using bacterially expressed D. melanogaster EcR/USP receptor proteins. The 11alpha-acyl derivatives do retain a significant amount of biological activity relative to the parent ecdysteroid. Further, although activity initially drops with the extension of the acyl chain length (C2 to C4, it then increases (C6 to C10, before decreasing again (C14 and C20. The implications of these findings for the interaction of ecdysteroids with the ecdysteroid receptor and potential applications in the generation of affinity-labelled and fluorescently-tagged ecdysteroids are discussed.

  15. Turnover and metabolism of phosphatidylglycerol acyl moieties in E. coli

    Fatty acids synthesized in mutants (plsB) blocked in de novo phospholipid biosynthesis were preferentially transferred to phosphatidylglycerol (PtdGro). The ratio of phospholipid species labeled with 32P and [3H]acetate in the absence of glycerol-3-P acyltransferase activity indicated that [3H]acetate incorporation into PtdGro was due to fatty acid turnover. The magnitude of the turnover process was difficult to estimate due to a significant contraction of the acetyl-CoA pool following the inhibition of phospholipid synthesis. A possible connection between PtdGro turnover and protein acylation was investigated in an E. coli strain containing a lipoprotein expression vector. Cells were prelabeled with [3H]acetate and lipoprotein expression was induced concomitant with the addition of exogenous [14C]-palmitate. [14C] Palmitate was assimilated into the l-position of phosphatidylethanolamine and transferred to the amino terminus of the lipoprotein. In contrast, the ester-linked lipoprotein fatty acids and PtdGro were not enriched in carbon-14 implying a metabolic relationship between these two pools. The data suggest that turnover of PtdGro acyl moieties is related to protein acylation, but a direct link between the two processes remains to be established

  16. Metabolism of acyl-lipids in Chlamydomonas reinhardtii.

    Li-Beisson, Yonghua; Beisson, Fred; Riekhof, Wayne

    2015-05-01

    Microalgae are emerging platforms for production of a suite of compounds targeting several markets, including food, nutraceuticals, green chemicals, and biofuels. Many of these products, such as biodiesel or polyunsaturated fatty acids (PUFAs), derive from lipid metabolism. A general picture of lipid metabolism in microalgae has been deduced from well characterized pathways of fungi and land plants, but recent advances in molecular and genetic analyses of microalgae have uncovered unique features, pointing out the necessity to study lipid metabolism in microalgae themselves. In the past 10 years, in addition to its traditional role as a model for photosynthetic and flagellar motility processes, Chlamydomonas reinhardtii has emerged as a model organism to study lipid metabolism in green microalgae. Here, after summarizing data on total fatty acid composition, distribution of acyl-lipid classes, and major acyl-lipid molecular species found in C. reinhardtii, we review the current knowledge on the known or putative steps for fatty acid synthesis, glycerolipid desaturation and assembly, membrane lipid turnover, and oil remobilization. A list of characterized or putative enzymes for the major steps of acyl-lipid metabolism in C. reinhardtii is included, and subcellular localizations and phenotypes of associated mutants are discussed. Biogenesis and composition of Chlamydomonas lipid droplets and the potential importance of lipolytic processes in increasing cellular oil content are also highlighted. PMID:25660108

  17. New players in the fatty acyl ethanolamide metabolism.

    Rahman, Iffat Ara Sonia; Tsuboi, Kazuhito; Uyama, Toru; Ueda, Natsuo

    2014-08-01

    Fatty acyl ethanolamides represent a class of endogenous bioactive lipid molecules and are generally referred to as N-acylethanolamines (NAEs). NAEs include palmitoylethanolamide (anti-inflammatory and analgesic substance), oleoylethanolamide (anorexic substance), and anandamide (endocannabinoid). The endogenous levels of NAEs are mainly regulated by enzymes responsible for their biosynthesis and degradation. In mammalian tissues, the major biosynthetic pathway starts from glycerophospholipids and is composed of two enzyme reactions. The first step is N-acylation of ethanolamine phospholipids catalyzed by Ca(2+)-dependent N-acyltransferase and the second step is the release of NAEs from N-acylated ethanolamine phospholipids by N-acylphosphatidylethanolamine (NAPE)-hydrolyzing phospholipase D (NAPE-PLD). As for the degradation of NAEs, fatty acid amide hydrolase plays the central role. However, recent studies strongly suggest the involvement of other enzymes in the NAE metabolism. These enzymes include members of the HRAS-like suppressor family (also called phospholipase A/acyltransferase family), which were originally discovered as tumor suppressors but can function as Ca(2+)-independent NAPE-forming N-acyltransferases; multiple enzymes involved in the NAPE-PLD-independent multi-step pathways to generate NAE from NAPE, which came to light by the analysis of NAPE-PLD-deficient mice; and a lysosomal NAE-hydrolyzing acid amidase as a second NAE hydrolase. These newly recognized enzymes may become the targets for the development of new therapeutic drugs. Here, we focus on recent enzymological findings in this area. PMID:24747663

  18. Cardiolipin molecular species with shorter acyl chains accumulate in Saccharomyces cerevisiae mutants lacking the acyl coenzyme A-binding protein Acb1p: new insights into acyl chain remodeling of cardiolipin.

    Rijken, Pieter J; Houtkooper, Riekelt H; Akbari, Hana; Brouwers, Jos F; Koorengevel, Martijn C; de Kruijff, Ben; Frentzen, Margrit; Vaz, Frédéric M; de Kroon, Anton I P M

    2009-10-01

    The function of the mitochondrial phospholipid cardiolipin (CL) is thought to depend on its acyl chain composition. The present study aims at a better understanding of the way the CL species profile is established in Saccharomyces cerevisiae by using depletion of the acyl-CoA-binding protein Acb1p as a tool to modulate the cellular acyl chain content. Despite the presence of an intact CL remodeling system, acyl chains shorter than 16 carbon atoms (C16) were found to accumulate in CL in cells lacking Acb1p. Further experiments revealed that Taz1p, a key CL remodeling enzyme, was not responsible for the shortening of CL in the absence of Acb1p. This left de novo CL synthesis as the only possible source of acyl chains shorter than C16 in CL. Experiments in which the substrate specificity of the yeast cardiolipin synthase Crd1p and the acyl chain composition of individual short CL species were investigated, indicated that both CL precursors (i.e. phosphatidylglycerol and CDP-diacylglycerol) contribute to comparable extents to the shorter acyl chains in CL in acb1 mutants. Based on the findings, we conclude that the fatty acid composition of mature CL in yeast is governed by the substrate specificity of the CL-specific lipase Cld1p and the fatty acid composition of the Taz1p substrates. PMID:19656950

  19. Exogenous myristic acid can be partially degraded prior to activation to form acyl-acyl carrier protein intermediates and lipid A in Vibrio harveyi.

    Shen, Z; Byers, D M

    1994-01-01

    To study the involvement of acyl carrier protein (ACP) in the metabolism of exogenous fatty acids in Vibrio harveyi, cultures were incubated in minimal medium with [9,10-3H]myristic acid, and labeled proteins were analyzed by gel electrophoresis. Labeled acyl-ACP was positively identified by immunoprecipitation with anti-V. harveyi ACP serum and comigration with acyl-ACP standards and [3H]beta-alanine-labeled bands on both sodium dodecyl sulfate- and urea-polyacrylamide gels. Surprisingly, most of the acyl-ACP label corresponded to fatty acid chain lengths of less than 14 carbons: C14, C12, C10, and C8 represented 33, 40, 14, and 8% of total [3H]14:0-derived acyl-ACPs, respectively, in a dark mutant (M17) of V. harveyi which lacks myristoyl-ACP esterase activity; however, labeled 14:0-ACP was absent in the wild-type strain. 14:0- and 12:0-ACP were also the predominant species labeled in complex medium. In contrast, short-chain acyl-ACPs ( or = C8) labeled with [3H]beta-alanine fivefold, while total incorporation of [3H]14:0 was not affected, although a shift to shorter chain lengths was noted. Additional bands which comigrated with acyl-ACP on sodium dodecyl sulfate gels were identified as lipopolysaccharide by acid hydrolysis and thin-layer chromatography. The levels of incorporation of [3H] 14:0 into acyl-ACP and lipopolysaccharide were 2 and 15%, respectively, of that into phospholipid by 10 min. Our results indicate that in contrast to the situation in Escherichia coli, exogenous fatty acids can be activated to acyl-ACP intermediates after partial degradation in V. harveyi and can effectively label products (i.e., lipid A) that require ACP as an acyl donor. Images PMID:8282714

  20. N-Acyl amino acids and N-acyl neurotransmitter conjugates: neuromodulators and probes for new drug targets

    Connor, Mark; Vaughan, Chris W; Vandenberg, Robert J.

    2010-01-01

    The myriad functions of lipids as signalling molecules is one of the most interesting fields in contemporary pharmacology, with a host of compounds recognized as mediators of communication within and between cells. The N-acyl conjugates of amino acids and neurotransmitters (NAANs) have recently come to prominence because of their potential roles in the nervous system, vasculature and the immune system. NAAN are compounds such as glycine, GABA or dopamine conjugated with long chain fatty acids...

  1. Expression of structural genes related to anthocyanin biosynthesis of Vitis amurensis

    Quan Zhao; Fei He; Malcolm J Reeves; Qiu-Hong Pan; Chang-Qing Duan; Jun Wang

    2016-01-01

    This research was designed to assess the changes in anthocyanin content in grape skins of Vitis amurensis and to explore mRNA transcriptions of 11 structural genes (PAL, CHS3, CHI1, F3H2, F30H, F3050H, DFR, LDOX, UFGT, OMT and GST) related to anthocyanin biosynthesis during grape berry development, by the use of HPLC-MS/MS and real-time Q-PCR analysis. Accumulation of anthocyanins began at veraison, continued throughout the later berry development and reached a peak at maturity. Veraison is the time when the berries turn from green to purple. Expression of PAL, CHI1, and LDOX were up-regulated from 2 to 4 weeks after flowering (WAF), down-regulated from 6 WAF to veraison, whereas DFR was up-regulated at 8 WAF, and then up-regulated from veraison to maturity. CHS3, F3050H, UFGT, GST, and OMT were down-regulated from 2 WAF to veraison, and then up-regulated from veraison to maturity. The transcriptional expressions of the 11 structural genes also showed positive correlations with the anthocyanin content from veraison to maturity. Positive correlations were also observed between OMT transcrip-tional level and the content of methoxyl-anthocyanins, and between F3050H transcriptional level and the content of delphinidin anthocyanins. F3H2 and F30H expression was up-regulated at 2 WAF. F3H2 expression was down-regu-lated from 4 WAF to veraison and then up-regulated again from veraison to maturity. F30H expression was down-reg-ulated at 4 WAF and then up-regulated again from 6 WAF to maturity. F30H transcriptional level was correlated posi-tively with the cyanidin anthocyanin concentration from veraison to maturity. These results indicate that the onset of anthocyanin synthesis during berry development coincides with a coordinated increase in the expression of a number of genes in the anthocyanin biosynthetic pathway.

  2. Suppression of acyl migration in enzymatic production of structured lipids through temperature programming

    Yang, Tiankui; Fruekilde, Maj-Britt; Xu, Xuebing

    2005-01-01

    considerably inhibited in the temperature-programmed acidolysis of PPP with CLA or CA, with only slight reduction of acyl incorporation, the reaction leading to the required products. Acyl migration was reduced by 29% (35 h) and 45% (48 h), respectively, in the acidolysis of PPP with CLA under solvent and......Acyl migration in the glycerol backbone often leads to the increase of by-products in the enzymatic production of specific structured lipids. Acyl migration is a thermodynamic process and is very difficult to stop fully in actual reactions. The objective of this study was to investigate the...... feasibility of suppressing acyl migration by a programmed change of reaction temperature without loss of reaction yield. The model reactions were the acidolysis of tripalmitin with conjugated linoleic acid (CLA) or with caprylic acid (CA) targeted for human milk fat substitutes. Acyl migration was...

  3. Characterization of new glycolipid biosurfactants, tri-acylated mannosylerythritol lipids, produced by Pseudozyma yeasts.

    Fukuoka, Tokuma; Morita, Tomotake; Konishi, Masaaki; Imura, Tomohiro; Kitamoto, Dai

    2007-07-01

    Mannosylerythritol lipids (MELs) are glycolipid biosurfactants produced by Pseudozyma yeasts. They show not only the excellent interfacial properties but also versatile biochemical actions. In the course of MEL production from soybean oil by P. antarctica and P. rugulosa, some new extracellular glycolipids (more hydrophobic than the previously reported di-acylated MELs) were found in the culture medium. The most hydrophobic one was identified as 1-O-alka(e)noyl-4-O-[(4',6'-di-O-acetyl-2',3'-di-O-alka(e)noyl)-beta-D-mannopyranosyl]-D-erythritol, namely tri-acylated MEL. Others were tri-acylated MELs bearing only one acetyl group. The tri-acylated MEL could be prepared by the lipase-catalyzed esterification of a di-acylated MEL with oleic acid implying that the new glycolipids are synthesized from di-acylated MELs in the culture medium containing the residual fatty acids. PMID:17417694

  4. The Tomato Hoffman’s Anthocyaninless Gene Encodes a bHLH Transcription Factor Involved in Anthocyanin Biosynthesis That Is Developmentally Regulated and Induced by Low Temperatures

    Zhengkun Qiu; Xiaoxuan Wang; Jianchang Gao; Yanmei Guo; Zejun Huang; Yongchen Du

    2016-01-01

    Anthocyanin pigments play many roles in plants, including providing protection against biotic and abiotic stresses. Many of the genes that mediate anthocyanin accumulation have been identified through studies of flowers and fruits; however, the mechanisms of genes involved in anthocyanin regulation in seedlings under low-temperature stimulus are less well understood. Genetic characterization of a tomato inbred line, FMTT271, which showed no anthocyanin pigmentation, revealed a mutation in a b...

  5. LcMYB1 Is a Key Determinant of Differential Anthocyanin Accumulation among Genotypes, Tissues, Developmental Phases and ABA and Light Stimuli in Litchi chinensis

    Lai, Biao; Li, Xiao-Jing; Hu, Bing; Qin, Yong-Hua; Huang, Xu-Ming; Wang, Hui-Cong; Hu, Gui-Bing

    2014-01-01

    The red coloration of litchi fruit depends on the accumulation of anthocyanins. The anthocyanins level in litchi fruit varies widely among cultivars, developmental stages and environmental stimuli. Previous studies on various plant species demonstrate that anthocyanin biosynthesis is controlled at the transcriptional level. Here, we describe a litchi R2R3-MYB transcription factor gene, LcMYB1, which demonstrates a similar sequence as other known anthocyanin regulators. The transcription level...

  6. Analysis and characterization of anthocyanins and carotenoids in Japanese blue tomato.

    Ooe, Emi; Ogawa, Kenjirou; Horiuchi, Tadashi; Tada, Hiroyuki; Murase, Hiromi; Tsuruma, Kazuhiro; Shimazawa, Masamitsu; Hara, Hideaki

    2016-01-01

    Tomato (Solanum lycopersicum) is rich in anthocyanins, which are polyphenolic pigments. This study aimed to analyze and characterize the anthocyanin composition in cultivated blue tomato in Japan. The extracts of peel, seed, and pulp of tomatoes were purified following which anthocyanins and lycopene contents were analyzed using high-performance liquid chromatography and electrospray ionization mass spectrometry. Eleven types of anthocyanins were identified, including delphinidin, petunidin, and malvidin. Further, the antioxidant activity of anthocyanins was evaluated using 2,2'-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid) diammonium salt radical quenching assays and electron spin resonance. "Blue tomato" extracts exert antioxidant activity. Thus, we showed that petunidin was present in the "blue tomato" peel while lycopene was present in the peel and pulp. Additionally, the blue tomato peel extract was found to significantly inhibit H2O2-induced cell death in vitro. This is the first study on cell protective effects of Japanese blue tomato extract and petunidin in murine photoreceptor cells. PMID:26443075

  7. Analytical standards production for the analysis of pomegranate anthocyanins by HPLC

    Manuela Cristina Pessanha de Araújo Santiago

    2014-03-01

    Full Text Available Pomegranate (Punica granatum L. is a fruit with a long medicinal history, especially due to its phenolic compounds content, such as the anthocyanins, which are reported as one of the most important natural antioxidants. The analysis of the anthocyanins by high performance liquid chromatography (HPLC can be considered as an important tool to evaluate the quality of pomegranate juice. For research laboratories the major challenge in using HPLC for quantitative analyses is the acquisition of high purity analytical standards, since these are expensive and in some cases not even commercially available. The aim of this study was to obtain analytical standards for the qualitative and quantitative analysis of the anthocyanins from pomegranate. Five vegetable matrices (pomegranate flower, jambolan, jabuticaba, blackberry and strawberry fruits were used to isolate each of the six anthocyanins present in pomegranate fruit, using an analytical HPLC scale with non-destructive detection, it being possible to subsequently use them as analytical standards. Furthermore, their identities were confirmed by high resolution mass spectrometry. The proposed procedure showed that it is possible to obtain analytical standards of anthocyanins with a high purity grade (98.0 to 99.9% from natural sources, which was proved to be an economic strategy for the production of standards by laboratories according to their research requirements.

  8. The anti-photooxidation of anthocyanins-rich leaves of a purple rice cultivar

    PENG; Changlian; LIN; Guizhu; LIN; Zhifang; CHEN; Shaowei

    2006-01-01

    In the leaf of rice (Oryza sativa L.) cultivar Yunnan purple rice, the anthocyanins with an obvious absorption peak at 530nm were distributed in the cells of upper and lower epidermis, bulliform tissue and bristle. The maximal photosynthetic oxygen evolution rate and chlorophyll content in flag leaves were 28% and 23%, respectively, more than the common green leaf rice cultivar Chijiaoruanzhan. Higher chlorophyll content is probably one of the physiological adaptations for enhancing light harvesting capacity of the antenna in photosystems in this cyanic leaves species. Upon the photooxidation of leaf segments mediated by methyl viologen in weak light for 3 days, the distinct bleaching of anthocyanins in purple rice was associated with the reduction of scavenging ability to DPPH· free radical ability and the increase in membrane leakage rate. But almost no changes in contents of flavonoids and total phenolics were observed. Chlorophyll fluorescence parameters Fv/Fo, qP and фPSII decreased with the increase in NPQ and DES of xanthophylls cycle after photooxidation treatment. Green rice leaves showed more decrease in DPPH· scavenging rate and more increase in cell membrane leakage rate but showed a trace of anthocyanins during photooxidation. It is suggested that anthocyanin may be a beneficial and primary antioxidant in sun cyanic rice leaves against oxidative stress induced by environmental adversity. And photooxidation could induce different changing patterns of anthocyanins between the tested purple and green rice leaves.

  9. Investigation of optical properties of anthocyanin doped into sol-gel based matrix

    Hashim, Hasrina; Abdul Aziz, Nik Mohd Azmi Nik; Isnin, Aishah

    2012-06-01

    Anthocyanin dye was extracted from petal of Hibiscus rosasinensis (Bunga Raya) and doped into sol-gel based matrix to investigate an effect of pH change on its optical properties. Sol-gel matrix based on Vinyl triethoxysilene (VTES) as a precursor was prepared through Sol-gel process at pH 7. The sol was doped with 0.1% of Anthocyanin and the same amount of dye was also dissolved in ethanol as a comparative sample. Hydrochloric Acid, HCl and Tetramethylammonium Hydroxide, TMAH were used to change the pH value by adding them at various concentrations into each sample. The emission spectra and chemical structures of the samples were measured by Spectrofluorometer and Fourier Transform Infrared (FTIR) respectively. When excited at 410 nm, two emission peaks at about 492 and 574 nm were observed for Anthocyanin in acidic environment both in ethanol and VTES sol. In base environment however, only Anthocyanin dissolved in ethanol produced emission peak with a single peak at about 539 nm. The sensitivity of Anthocyanin dye toward pH changes in VTES open a possibility to use it as sensing element in which sol-gel based matrix are known to have higher mechanical strength and thermal stability.

  10. Sugar Maple Pigments Through the Fall and the Role of Anthocyanin as an Analytical Tool

    Lindgren, E.; Rock, B.; Middleton, E.; Aber, J.

    2008-12-01

    Sugar maple habitat is projected to almost disappear in future climate scenarios. In fact, many institutions state that these trees are already in decline. Being able to detect sugar maple health could prove to be a useful analytical tool to monitor changes in phenology. Anthocyanin, a red pigment found in sugar maples, is thought to be a universal indicator of plant stress. It is very prominent in the spring during the first flush of leaves, as well as in the fall as leaves senesce. Determining an anthocyanin index that could be used with satellite systems will provide a greater understanding of tree phenology and the distribution of plant stress, both over large areas as well as changes over time. The utilization of anthocyanin for one of it's functions, prevention of oxidative stress, may fluctuate in response to changing climatic conditions that occur during senescence or vary from year to year. By monitoring changes in pigment levels and antioxidant capacity through the fall, one may be able to draw conclusions about the ability to detect anthocyanin remotely from space-based systems, and possibly determine a more specific function for anthocyanin during fall senescence. These results could then be applied to track changes in tree stress.

  11. Anthocyanins degradation during storage of Hibiscus sabdariffa extract and evolution of its degradation products.

    Sinela, André; Rawat, Nadirah; Mertz, Christian; Achir, Nawel; Fulcrand, Hélène; Dornier, Manuel

    2017-01-01

    Degradation parameters of two main anthocyanins from roselle extract (Hibiscus sabdariffa L.) stored at different temperatures (4-37°C) over 60days were determined. Anthocyanins and some of their degradation products were monitored and quantified using HPLC-MS and DAD. Degradation of anthocyanins followed first-order kinetics and reaction rate constants (k values), which were obtained by non-linear regression, showed that the degradation rate of delphinidin 3-O-sambubioside was higher than that of cyanidin 3-O-sambubioside with k values of 9.2·10(-7)s(-1) and 8.4·10(-7)s(-1) at 37°C respectively. The temperature dependence of the rate of anthocyanin degradation was modeled by the Arrhenius equation. Degradation of delphinidin 3-O-sambubioside (Ea=90kJmol(-1)) tended to be significantly more sensitive to an increase in temperature than cyanidin 3-O-sambubioside (Ea=80kJmol(-1)). Degradation of these anthocyanins formed scission products (gallic and protocatechuic acids respectively) and was accompanied by an increase in polymeric color index. PMID:27507471

  12. Molecular characterization and expression analyses of an anthocyanin synthase gene from Magnolia sprengeri Pamp.

    Shi, Shou-Guo; Li, Shan-Ju; Kang, Yong-Xiang; Liu, Jian-Jun

    2015-01-01

    Anthocyanin synthase (ANS), which catalyzes the conversion of colorless leucoanthocyanins into colored anthocyanins, is a key enzyme in the anthocyanin biosynthetic pathway. It plays important roles in plant development and defense. An ANS gene designated as MsANS was cloned from Magnolia sprengeri using rapid amplification of complementary DNA (cDNA) ends technology. The full-length MsANS is 1171-bp long and contains a 1080-bp open reading frame encoding a 360 amino acid polypeptide. In a sequence alignment analysis, the deduced MsANS protein showed high identity to ANS proteins from other plants: Prunus salicina var. cordata (74 % identity), Ampelopsis grossedentata (74 % identity), Pyrus communis (73 % identity), and Prunus avium (73 % identity). A structural analysis showed that MsANS belongs to 2-oxoglutarate (2OG)- and ferrous iron-dependent oxygenase family because it contains three binding sites for 2OG. Real-time quantitative polymerase chain reaction analyses showed that the transcript level of MsANS was 26-fold higher in red petals than in white petals. The accumulation of anthocyanins in petals of white, pink, and red M. sprengeri flowers was analyzed by HPLC. The main anthocyanin was cyanidin-3-o-glucoside chloride, and the red petals contained the highest concentration of this pigment. PMID:25315387

  13. Arabidopsis CAPRICE (MYB and GLABRA3 (bHLH control tomato (Solanum lycopersicum anthocyanin biosynthesis.

    Takuji Wada

    Full Text Available In Arabidopsis thaliana the MYB transcription factor CAPRICE (CPC and the bHLH transcription factor GLABRA3 (GL3 are central regulators of root-hair differentiation and trichome initiation. By transforming the orthologous tomato genes SlTRY (CPC and SlGL3 (GL3 into Arabidopsis, we demonstrated that these genes influence epidermal cell differentiation in Arabidopsis, suggesting that tomato and Arabidopsis partially use similar transcription factors for epidermal cell differentiation. CPC and GL3 are also known to be involved in anthocyanin biosynthesis. After transformation into tomato, 35S::CPC inhibited anthocyanin accumulation, whereas GL3::GL3 enhanced anthocyanin accumulation. Real-time reverse transcription PCR analyses showed that the expression of anthocyanin biosynthetic genes including Phe-ammonia lyase (PAL, the flavonoid pathway genes chalcone synthase (CHS, dihydroflavonol reductase (DFR, and anthocyanidin synthase (ANS were repressed in 35S::CPC tomato. In contrast, the expression levels of PAL, CHS, DFR, and ANS were significantly higher in GL3::GL3 tomato compared with control plants. These results suggest that CPC and GL3 also influence anthocyanin pigment synthesis in tomato.

  14. Influence of Temperature and Preserving Agents on the Stability of Cornelian Cherries Anthocyanins

    Bianca Moldovan

    2014-06-01

    Full Text Available 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.

  15. Bioavailability of anthocyanins and colonic polyphenol metabolites following consumption of aronia berry extract.

    Xie, Liyang; Lee, Sang Gil; Vance, Terrence M; Wang, Ying; Kim, Bohkyung; Lee, Ji-Young; Chun, Ock K; Bolling, Bradley W

    2016-11-15

    A single-dose pharmacokinetic trial was conducted in 6 adults to evaluate the bioavailability of anthocyanins and colonic polyphenol metabolites after consumption of 500mg aronia berry extract. UHPLC-MS methods were developed to quantitate aronia berry polyphenols and their metabolites in plasma and urine. While anthocyanins were bioavailable, microbial phenolic catabolites increased ∼10-fold more than anthocyanins in plasma and urine. Among the anthocyanins, cyanidin-3-O-galactoside was rapidly metabolized to peonidin-3-O-galactoside. Aronia polyphenols were absorbed and extensively metabolized with tmax of anthocyanins and other polyphenol catabolites from 1.0h to 6.33h in plasma and urine. Despite significant inter-individual variation in pharmacokinetic parameters, concentrations of polyphenol metabolites in plasma and urine at 24h were positively correlated with total AUC in plasma and urine (r=0.93, and r=0.98, respectively). This suggests that fasting blood and urine collections could be used to estimate polyphenol bioavailability and metabolism after aronia polyphenol consumption. PMID:27283706

  16. The Dark-Purple Tea Cultivar 'Ziyan' Accumulates a Large Amount of Delphinidin-Related Anthocyanins.

    Lai, Yun-Song; Li, Sha; Tang, Qian; Li, Huan-Xiu; Chen, Shen-Xiang; Li, Pin-Wu; Xu, Jin-Yi; Xu, Yan; Guo, Xiang

    2016-04-01

    Recently, we developed a novel tea cultivar 'Ziyan' with distinct purple leaves. There was a significant correlation between leaf color and anthocyanin pigment content in the leaves. A distinct allocation of metabolic flow for B-ring trihydroxylated anthocyanins and catechins in 'Ziyan' was observed. Delphinidin, cyanidin, and pelargonidin (88.15 mg/100 g FW in total) but no other anthocyanin pigments were detected in 'Ziyan', and delphinidin (70.76 mg/100 g FW) was particularly predominant. An analysis of the catechin content in 'Ziyan' and eight other cultivars indicated that 'Ziyan' exhibits a preference for synthesizing B-ring trihydroxylated catechins (with a proportion of 74%). The full-length cDNA sequences of flavonoid pathway genes were isolated by RNA-Seq coupled with conventional TA cloning, and their expression patterns were characterized. Purple-leaved cultivars had lower amounts of total catechins, polyphenols, and water extract than ordinary non-anthocyanin cultivars but similar levels of caffeine. Because dark-purple-leaved Camellia species are rare in nature, this study provides new insights into the interplay between the accumulations of anthocyanins and other bioactive components in tea leaves. PMID:26996195

  17. Production of structured lipids: acyl migration during enzymatic interesterification and downstream processing

    Xu, Xuebing

    1997-01-01

    -2 position or sn-1,3 positions of glycerol backbone. These kinds of lipids are reported to be promising for both enteral and parenteral nutrition. However, acyl migration occurs in the reaction stage and downstream purification process. This side-reaction causes by-products which are harmful to the...... required products. In this paper, the reasons of acyl migration and factors affecting the acyl migration were reviewed and discussed. The possible solutions were also evaluated....

  18. Structural properties of pepsin-solubilized collagen acylated by lauroyl chloride along with succinic anhydride

    Li, Conghu [The Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu 610065 (China); College of Life Sciences, Anqing Normal University, Anqing 246011 (China); Tian, Zhenhua; Liu, Wentao [The Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu 610065 (China); Li, Guoying, E-mail: liguoyings@163.com [The Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu 610065 (China)

    2015-10-01

    The structural properties of pepsin-solubilized calf skin collagen acylated by lauroyl chloride along with succinic anhydride were investigated in this paper. Compared with native collagen, acylated collagen retained the unique triple helix conformation, as determined by amino acid analysis, circular dichroism and X-ray diffraction. Meanwhile, the thermostability of acylated collagen using thermogravimetric measurements was enhanced as the residual weight increased by 5%. With the temperature increased from 25 to 115 °C, the secondary structure of native and acylated collagens using Fourier transform infrared spectroscopy measurements was destroyed since the intensity of the major amide bands decreased and the positions of the major amide bands shifted to lower wavenumber, respectively. Meanwhile, two-dimensional correlation spectroscopy revealed that the most sensitive bands for acylated and native collagens were amide I and II bands, respectively. Additionally, the corresponding order of the groups between native and acylated collagens was different and the correlation degree for acylated collagen was weaker than that of native collagen, suggesting that temperature played a small influence on the conformation of acylated collagen, which might be concluded that the hydrophobic interaction improved the thermostability of collagen. - Highlights: • Acylated collagen retained the unique triple helix conformation. • Acylated collagen had stronger thermostability than native collagen. • Amide I was the most sensitive band to the temperature for acylated collagen. • Amide II was the most sensitive band to the temperature for native collagen. • Auto-peak at 1680 cm{sup −1} for acylated collagen disappeared at higher temperature.

  19. Slow Onset Inhibition of Bacterial β-Ketoacyl-acyl Carrier Protein Synthases by Thiolactomycin*

    Machutta, Carl A.; Bommineni, Gopal R.; Luckner, Sylvia R.; Kapilashrami, Kanishk; Ruzsicska, Bela; Simmerling, Carlos; Kisker, Caroline; Tonge, Peter J.

    2009-01-01

    Thiolactomycin (TLM), a natural product thiolactone antibiotic produced by species of Nocardia and Streptomyces, is an inhibitor of the β-ketoacyl-acyl carrier protein synthase (KAS) enzymes in the bacterial fatty acid synthase pathway. Using enzyme kinetics and direct binding studies, TLM has been shown to bind preferentially to the acyl-enzyme intermediates of the KASI and KASII enzymes from Mycobacterium tuberculosis and Escherichia coli. These studies, which utilized acyl-enzyme mimics in...

  20. The co-pigmentation of anthocyanin isolated from mangosteen pericarp (Garcinia Mangostana L.) as Natural Dye for Dye- Sensitized Solar Cells (DSSC)

    Munawaroh, H.; adillah, G. F.; Saputri, L. N. M. Z.; Hanif, Q. A.; Hidayat, R.; Wahyuningsih, S.

    2016-02-01

    Study of color stability of anthocyanin from extract mangosteen pericarp (Garcinia mangostana L.) with co-pigmentation method has been conducted. Malic acid and ascorbic acid used as a co-pigment to stabilize the anthocyanin structure through formation of new binding between anthocyanin. Anthocyanin from mangosteen pericarp were isolated by several steps, including maceration, extraction, and Thin Layer Chromatography (TLC). The anthocyanin separation was conducted by TLC, while the identification of functional groups of those compound, were used FTIR (Fourier Transform Infrared Spectroscopy) for spectra analysis. Ultraviolet- visible absorption spectra have represented differences absorbance and color intensity in various pH. Copigmentation with malic acid and ascorbic acid in many composition and temperature were also well described. Meanwhile, anthocyanin-malic acid and anthocyanin-ascorbic acid have color retention higher than that of pure anthocyanin. Maximum color retention has been achieved at a ratio of 1:3 and 1:5 for ascorbic acid and malic acid, respectively. Therefore, the addition of ascorbic acid and malic acid as a copigment shows the ability to protect color retention of anthocyanin (mangosteen pericarp) from degradation process. The better efficiency of DSSC (η) have been achieved, whereas n of controlled anthocyanin, anthocyanin-ascorbic acid, and anthocyanin-malic acid were 0,1996%, 0,2922%, 0,3029%, respectively.

  1. High-purity isolation of anthocyanins mixtures from fruits and vegetables--a novel solid-phase extraction method using mixed mode cation-exchange chromatography.

    He, Jian; Giusti, M Monica

    2011-11-01

    Research on biological activity of anthocyanins requires the availability of high purity materials. However, current methods to isolate anthocyanins or anthocyanin mixtures are tedious and expensive or insufficient for complete isolation. We applied a novel cation-exchange/reversed-phase combination solid-phase extraction (SPE) technique, and optimized the use of water/organic buffer mobile phases to selectively separate anthocyanins. Crude extracts of various representative anthocyanin sources were purified with this technique and compared to 3 commonly used SPE techniques: C(18), HLB, and LH-20. Purified anthocyanin fractions were analyzed with high performance liquid chromatography (HPLC) coupled to photodiode array (PDA) and mass spectrometry (MS) detectors and by Fourier transform infrared (FT-IR) spectroscopy. The UV-visible chromatograms quantitatively demonstrated that our novel technique achieved significantly higher (Pmethod, for 11 of the 12 anthocyanin sources tested. Among them, eight were purified to greater than 99% purity (based on UV-visible chromatograms). The new method efficiently removed non-anthocyanin phenolics. MS and FT-IR results semi-quantitatively confirmed extensive reduction of impurities. Due to strong ionic interaction, our sorbent capacity was superior to others, resulting in the highest throughput and least use of organic solvents. This new methodology for isolation of anthocyanin mixtures drastically increased purity and efficiency while maintaining excellent recovery rate and low cost. The availability of high purity anthocyanin mixtures will facilitate anthocyanin studies and promote the application of anthocyanins in the food and nutraceutical industries. PMID:21968344

  2. Paper Chromatography and UV-Vis Spectroscopy to Characterize Anthocyanins and Investigate Antioxidant Properties in the Organic Teaching Laboratory

    Galloway, Kelli R.; Bretz, Stacey Lowery; Novak, Michael

    2015-01-01

    A variety of fruits and vegetables, including raspberries, blueberries, Concord grapes, blackberries, strawberries, peaches, eggplant, red cabbage, and red onions, contain flavonoid compounds known as anthocyanins that are responsible for the blue-red color and the astringent taste associated with such foods. In addition, anthocyanins exhibit a…

  3. Anthocyanin-Rich Juice Lowers Serum Cholesterol, Leptin, and Resistin and Improves Plasma Fatty Acid Composition in Fischer Rats.

    Daniela Graf

    Full Text Available Obesity and obesity-associated diseases e.g. cardiovascular diseases and type 2 diabetes are spread worldwide. Anthocyanins are supposed to have health-promoting properties, although convincing evidence is lacking. The aim of the present study was to investigate the effect of anthocyanins on several risk factors for obesity-associated diseases. Therefore, Fischer rats were fed anthocyanin-rich grape-bilberry juice or an anthocyanin-depleted control juice for 10 weeks. Intervention with anthocyanin-rich grape-bilberry juice reduced serum cholesterol and tended to decrease serum triglycerides. No effects were seen for serum non-esterified fatty acids, glucose, and insulin. Anthocyanin-rich grape-bilberry juice intervention reduced serum leptin and resistin, but showed no influence on serum adiponectin and secretion of adipokines from mesenteric adipose tissue. Furthermore, anthocyanin-rich grape-bilberry juice increased the proportion of polyunsaturated fatty acids and decreased the amount of saturated fatty acids in plasma. These results indicate that anthocyanins possess a preventive potential for obesity-associated diseases.

  4. Glucose Sensor MdHXK1 Phosphorylates and Stabilizes MdbHLH3 to Promote Anthocyanin Biosynthesis in Apple.

    Hu, Da-Gang; Sun, Cui-Hui; Zhang, Quan-Yan; An, Jian-Ping; You, Chun-Xiang; Hao, Yu-Jin

    2016-08-01

    Glucose induces anthocyanin accumulation in many plant species; however, the molecular mechanism involved in this process remains largely unknown. Here, we found that apple hexokinase MdHXK1, a glucose sensor, was involved in sensing exogenous glucose and regulating anthocyanin biosynthesis. In vitro and in vivo assays suggested that MdHXK1 interacted directly with and phosphorylated an anthocyanin-associated bHLH transcription factor (TF) MdbHLH3 at its Ser361 site in response to glucose. Furthermore, both the hexokinase_2 domain and signal peptide are crucial for the MdHXK1-mediated phosphorylation of MdbHLH3. Moreover, phosphorylation modification stabilized MdbHLH3 protein and enhanced its transcription of the anthocyanin biosynthesis genes, thereby increasing anthocyanin biosynthesis. Finally, a series of transgenic analyses in apple calli and fruits demonstrated that MdHXK1 controlled glucose-induced anthocyanin accumulation at least partially, if not completely, via regulating MdbHLH3. Overall, our findings provide new insights into the mechanism of the glucose sensor HXK1 modulation of anthocyanin accumulation, which occur by directly regulating the anthocyanin-related bHLH TFs in response to a glucose signal in plants. PMID:27560976

  5. The beet Y locus encodes an anthocyanin-MYB-like protein that activates the betalain red pigment pathway

    Almost all flowering plants produce red/violet, phenylalanine-based, anthocyanin pigments. A single order, the Caryophyllales, contains families that replace anthocyanins with tyrosine-based red and yellow betalain pigments. Close biological correlation of pigmentation patterns suggested that betala...

  6. CPC,a Single-Repeat R3 MYB,Is a Negative Regulator of Anthocyanin Biosynthesis in Arabidopsis

    Hui-Fen Zhu; Karen Fitzsimmons; Abha Khandelwal; Robert G.Kranz

    2009-01-01

    Single-repeat R3 MYB transcription factors like CPC (CAPRICE) are known to play roles in developmental processes such as root hair differentiation and trichome initiation.However,none of the six Arabidopsis single-repeat R3 MYB members has been reported to regulate flavonoid biosynthesis.We show here that CPC is a negative regulator of anthocyanin biosynthesis.In the process of using CPC to test GAL4-dependent driver lines,we observed a repression of anthocyanin synthesis upon GAL4-mediated CPC overexpression,We demonstrated that this is not due to an increase in nutrient uptake because of more root hairs.Rather,CPC expression level tightly controls anthocyanin accumulation.Microarray analysis on the whole genome showed that,of 37 000 features tested,85 genes are repressed greater than three-fold by CPC overexpression.Of these 85,seven are late anthocyanin biosynthesis genes.Also,anthocyanin synthesis genes were shown to be down-regulated in 35S::CPC overexpression plants.Transient expression results suggest that CPC competes with the R2R3-MYB transcription factor PAP1/2,which is an activator of anthocyanin biosynthesis genes.This report adds anthocyanin biosynthesis to the set of programs that are under CPC control,indicating that this regulator is not only for developmental programs (e.g.root hairs,trichomes),but can influence anthocyanin pigment synthesis.

  7. An R2R3 MYB transcription factor associated with regulation of the anthocyanin biosynthetic pathway in Rosaceae (on linr)

    Wang, Kui-Lin; Bolitho, Karen; Grafton, Karryn; Kortstee, A.J.; Karunairetnam, Sakuntala; McGhie, T.K.; Espley, R.V.; Hellens, R.P.; Allan, A.C.

    2010-01-01

    Background - The control of plant anthocyanin accumulation is via transcriptional regulation of the genes encoding the biosynthetic enzymes. A key activator appears to be an R2R3 MYB transcription factor. In apple fruit, skin anthocyanin levels are controlled by a gene called MYBA or MYB1, while the

  8. Possible regulatory role of phenylalanine ammonia-lyase in the production of anthocyanins in asparagus (Asparagus officinalis L)

    Flores, F.B.; Oosterhaven, J.; Martinez-Madrid, M.C.; Romojaro, F.

    2005-01-01

    The regulatory role of phenylalanine ammonia-lyase (PAL) in the light-induced accumulation of anthocyanins in the epidermis of asparagus spears has been analysed. A correlation between the stimulation of PAL activity and the rise in total anthocyanin content has been observed. Light radiation induce

  9. Gene regulation of anthocyanin biosynthesis in two blood-flesh peach (Prunus persica (L.) Batsch) cultivars during fruit development.

    Jiao, Yun; Ma, Rui-juan; Shen, Zhi-jun; Yan, Juan; Yu, Ming-liang

    2014-09-01

    The blood-flesh peach has become popular in China due to its attractive anthocyanin-induced pigmentation and antioxidant properties. In this study, we investigated the molecular mechanisms underlying anthocyanin accumulation by examining the expression of nine genes of the anthocyanin biosynthesis pathway found in the peach mesocarp. Expression was measured at six developmental stages in fruit of two blood-flesh and one white-flesh peach cultivars, using quantitative reverse transcription polymerase chain reaction (qRT-PCR). Results show that the expression of the chalcone synthase (CHS) gene was closely related to anthocyanin accumulation in both of the blood-flesh peaches. In the white-flesh peach, we found that the transcription level of phenylalanine ammonia-lyase (PAL) during fruit development was much lower than that in the blood-flesh peach, even though all other genes of the anthocyanin biosynthesis pathway were highly expressed, suggesting that the PAL gene may be limiting in anthocyanin production in the white-flesh peach. Moreover, the transcription levels of the CHS and UDP-glucose-flavonoid 3-O-glucosyltransferase (UFGT) genes were markedly up-regulated at three days after bag removal (DABR) in the blood-flesh peach, suggesting that CHS and UFGT are the key genes in the process of anthocyanin biosynthesis for both of the blood-flesh peaches. The present study will be of great help in improving understanding of the molecular mechanisms involved in anthocyanin accumulation in blood-flesh peaches. PMID:25183035

  10. Rapid Acyl-Homoserine Lactone Quorum Signal Biodegradation in Diverse Soils

    Ya-juan WANG; Leadbetter, Jared Renton

    2005-01-01

    Signal degradation impacts all communications. Although acyl-homoserine lactone (acyl-HSL) quorum-sensing signals are known to be degraded by defined laboratory cultures, little is known about their stability in nature. Here, we show that acyl-HSLs are biodegraded in soils sampled from diverse U.S. sites and by termite hindgut contents. When amended to samples at physiologically relevant concentrations, 14C-labeled acyl-HSLs were mineralized to 14CO2 rapidly and, at most sites examined, witho...

  11. Acyl-Acyl carrier protein regulates transcription of fatty acid biosynthetic genes via the FabT repressor in Streptococcus pneumoniae.

    Jerga, Agoston; Rock, Charles O

    2009-06-01

    Long-chain acyl-acyl carrier proteins (acyl-ACP) are established biochemical regulators of bacterial type II fatty acid synthases due to their ability to feedback-inhibit the early steps in the biosynthetic pathway. In Streptococcus pneumoniae, the expression of the fatty acid synthase (fab) genes is controlled by a helix-turn-helix transcriptional repressor called FabT. A screen of pathway intermediates identified acyl-ACP as a ligand that increased the affinity of FabT for DNA. FabT bound to a wide range of acyl-ACP chain lengths in the absence of DNA, but only the long-chain acyl-ACPs increase the affinity of FabT for DNA. FabT affinity for DNA increased with increasing acyl-ACP chain length with cis-vaccenoyl-ACP being the most effective ligand. Thus, FabT is a new ACP-interacting partner that acts as a transcriptional rheostat to fine tune the expression of the fab genes based on the demand for fatty acids. PMID:19376778

  12. Acyl-Acyl Carrier Protein Regulates Transcription of Fatty Acid Biosynthetic Genes via the FabT Repressor in Streptococcus pneumoniae*

    Jerga, Agoston; Rock, Charles O.

    2009-01-01

    Long-chain acyl-acyl carrier proteins (acyl-ACP) are established biochemical regulators of bacterial type II fatty acid synthases due to their ability to feedback-inhibit the early steps in the biosynthetic pathway. In Streptococcus pneumoniae, the expression of the fatty acid synthase (fab) genes is controlled by a helix-turn-helix transcriptional repressor called FabT. A screen of pathway intermediates identified acyl-ACP as a ligand that increased the affinity of FabT for DNA. FabT bound to a wide range of acyl-ACP chain lengths in the absence of DNA, but only the long-chain acyl-ACPs increase the affinity of FabT for DNA. FabT affinity for DNA increased with increasing acyl-ACP chain length with cis-vaccenoyl-ACP being the most effective ligand. Thus, FabT is a new ACP-interacting partner that acts as a transcriptional rheostat to fine tune the expression of the fab genes based on the demand for fatty acids. PMID:19376778

  13. Cardiolipin Molecular Species with Shorter Acyl Chains Accumulate in Saccharomyces cerevisiae Mutants Lacking the Acyl Coenzyme A-binding Protein Acb1p

    Rijken, Pieter J.; Houtkooper, Riekelt H.; Akbari, Hana; Brouwers, Jos F.; Koorengevel, Martijn C.; de Kruijff, Ben; Frentzen, Margrit; Vaz, Frédéric M.; de Kroon, Anton I. P. M.

    2009-01-01

    The function of the mitochondrial phospholipid cardiolipin (CL) is thought to depend on its acyl chain composition. The present study aims at a better understanding of the way the CL species profile is established in Saccharomyces cerevisiae by using depletion of the acyl-CoA-binding protein Acb1p as a tool to modulate the cellular acyl chain content. Despite the presence of an intact CL remodeling system, acyl chains shorter than 16 carbon atoms (C16) were found to accumulate in CL in cells lacking Acb1p. Further experiments revealed that Taz1p, a key CL remodeling enzyme, was not responsible for the shortening of CL in the absence of Acb1p. This left de novo CL synthesis as the only possible source of acyl chains shorter than C16 in CL. Experiments in which the substrate specificity of the yeast cardiolipin synthase Crd1p and the acyl chain composition of individual short CL species were investigated, indicated that both CL precursors (i.e. phosphatidylglycerol and CDP-diacylglycerol) contribute to comparable extents to the shorter acyl chains in CL in acb1 mutants. Based on the findings, we conclude that the fatty acid composition of mature CL in yeast is governed by the substrate specificity of the CL-specific lipase Cld1p and the fatty acid composition of the Taz1p substrates. PMID:19656950

  14. Anthocyanins increase low-density lipoprotein and plasma cholesterol and do not reduce atherosclerosis in Watanabe Heritable Hyperlipidemic rabbits

    Nielsen, I. L. F.; Rasmussen, S.E.; Mortensen, Alicja;

    2005-01-01

    Anthocyanin-rich beverages have shown beneficial effects on coronary heart disease in epidemiological and intervention studies. In the present study, we investigated the effect of black currant anthocyanins on atherosclerosis. Watanabe Heritable Hyperlipidemic rabbits (n = 61) were fed either a...... purified anthocyanin fraction front black currants, a black currant juice, probucol or control diet for 16 weeks. Purified anthocyanins significantly increased plasma cholesterol and low-density lipoprotein (LDL) cholesterol. Intake of black currant juice had no effect on total plasma cholesterol, but...... lowered very-low-density lipoprotein (VLDL) cholesterol significantly. There were no significant effects of either purified anthocyanins or black currant juice on aortic cholesterol or development of atherosclerosis after 16 weeks. Probucol had no effect on plasma cholesterol but significantly lowered...

  15. Liquid chromatographic-mass spectrometric analysis of anthocyanin composition of dark blue bee pollen from Echium plantagineum.

    Di Paola-Naranjo, Romina Daniela; Sánchez-Sánchez, José; González-Paramás, Ana María; Rivas-Gonzalo, Julián Carlos

    2004-10-29

    Dark blue bee pollen samples from pollinic type Echium plantegineum were analysed in order to identify and quantify their anthocyanin pigments. Five samples were collected from different apicultural Spanish regions and the anthocyanin composition was determined by HPLC with diode array and MS detection. Eight different pigments were identified, the principal anthocyanin being petunidin-3-O-rutinoside. The other pigments found were delphinidin, cyanidin and petunidin-3-O-glucoside; delphinidin, cyanidin, peonidin and malvidin-3-O-rutinoside and cyanidin-3-(6"-malonylglucoside). The anthocyanin content ranged from 45 to 80 mg/100 g of blue pollen, which could represent a significant source of phytochemicals. Minor variations in the anthocyanin profiles were found, which could be explained by the geographical differences between collection regions. PMID:15553145

  16. Carbohydrate nutrition and anthocyanin accumulation in light grown and etiolated shoot cultures of carob (Ceratonia siliqua L.

    Vinterhalter Branka

    2007-01-01

    Full Text Available Production of anthocyanins was studied in shoot cultures of carob at high (45.9 μmol s-1m-2 and low (9.2 μmol s-1m-2 irradiance levels and in darkness in relation to carbohydrate nutrition. Anthocyanin production was stimulated by light, but it also occurred in etiolated shoot cultures which developed in darkness. Anthocyanins were present in both leaves and shoot tips. The major factor affecting anthocyanin production was carbohydrate nutrition, with sucrose as a choice superior to fructose and glucose. The carbohydrate effect was clearly osmotic in nature, since anthocyanin production increased even at supraoptimal concentrations detrimental to the growth of shoot cultures. This conclusion was further confirmed in experiments in which sucrose was partly replaced with the sugar alcohols sorbitol and mannitol.

  17. Expression Analysis of Dihydroflavonol 4-Reductase Genes Involved in Anthocyanin Biosynthesis in Purple Grains of Wheat

    Mao-Sen LIU; Fang WANG; Yu-Xiu DONG; Xian-Sheng ZHANG

    2005-01-01

    The grain color of wheat (Triticum aestivum L.) is an important characteristic in crop production.Dihydroflavonol 4-reductase genes (DFR) encode the key enzyme dihydroflavonol 4-reductase, which is involved in the pigmentation of plant tissues. To investigate the molecular mechanism of anthocyanin deposition in grains of wheat, we determined the expression of the wheat DFR gene in purple grains of cultivar Heimai 76. The results showed that DFR transcripts were localized in the seed coat of purple grains rather than in the pericarp, whereas anthocyanins were accumulated in both tissues of purple grains,suggesting that anthocyanin deposition was mainly regulated at the transcriptional level. Overexpression of the TaDFR-A gene in Arabidopsis showed that TaDFR-A was responsible for the pigmentation of Arabidopsis plant tissues, indicating TaDFR-A gene has the same role in Arabidopsis.

  18. Optimization of Ultrasound-Assisted Extraction of Anthocyanins from Mulberry, Using Response Surface Methodology

    Ren-You Gan

    2011-05-01

    Full Text Available Mulberry is one of the most widely used traditional Chinese medicines. Anthocyanins are the main bioactive components of mulberry, and possess important biological activities, such as antimicrobial, anti-inflammatory and antioxidant activities. This study investigated the ultrasound-assisted extraction (UAE of anthocyanins from mulberry by using response surface methodology (RSM. The extraction conditions associated with anthocyanin yield, including extraction solvent, liquid-to-solid rate, temperature and extraction time, are discussed. The optimal conditions obtained by RSM for UAE from mulberry include 63.8% methanol contains 1% (v/v trifluoroacetic acid (TFA, 43.2 °C temperature, 23.8 (v/w liquid-to-solid ratio, and 40 min time for the maximum yield (64.70 ± 0.45 mg/g. The results indicated that the UAE can be an effective method for the extraction of some active components from plant materials.

  19. Anthocyanins, pigment stability and antioxidant activity in jabuticaba [Myrciaria cauliflora (Mart. O. Berg

    Annete de Jesus Boari Lima

    2011-09-01

    Full Text Available Different solvents were evaluated for the extraction of jabuticaba anthocyanin pigments, identifying, quantifying and verifying the stability of the anthocyanins, as well as the conduction of three antioxidant activity assays and determination of the vitamin C levels. The maceration with ethanol acidified with HCl 1.5 mol L-1 (85:15 provides better pigment extraction and stability. The skin is anthocyanin rich, presenting 1.59 and 2.06 g 100 g-1 of dry matter in the Paulista and Sabará varieties, respectively. Cyanidin 3-glucoside is the majority pigment of the skins, followed by delphinidin 3-glucoside. The highest level of vitamin C was found in the skins and seeds of both varieties. It was verified that the skins, presented more antioxidant activity, in free radical capture, as well as in retarding the lipid oxidation process.

  20. Light signaling induces anthocyanin biosynthesis via AN3 mediated COP1 expression

    Meng, Lai-Sheng; Liu, Aizhong

    2015-01-01

    Light signaling plays a pivotal role in controlling plant morphogenesis, metabolism, growth and development. The central process of light signaling pathway is to build the link between light signals and the expression of genes involved. Although studies focused on light signaling toward metabolism have been documented well in the past several decades, most regulation networks of light signaling in a specific metabolic production largely remained unknown. Anthocyanin accumulation in plant tissues depends on the availability of light signals, but only little is known about the potential regulation network underlying light signal controls anthocyanin biosynthesis. Here, we briefly review the recent progress on the light-triggered anthocyanin biosynthesis via ANGUSTIFOLIA3 (AN3) and CONSTITUTIVE PHOTOMORPHOGENIC1 (COP1) network in Arabidopsis. PMID:26357851

  1. Novel insight into the mechanism underlying light-controlled anthocyanin accumulation in eggplant (Solanum melongena L.).

    Jiang, Mingmin; Ren, Li; Lian, Hongli; Liu, Yang; Chen, Huoying

    2016-08-01

    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. PMID:27297989

  2. 拟南芥中花青素的修饰%Anthocyanin Modification in Arabidopsis

    谢烨; 孙毅; 黄继荣

    2013-01-01

    Anthocyanins are produced by a branch of the flavonoid pathway. They give plants a colorful world from red, purple to blue pigments, and play an important role in pollination and seed dispersal. The diversities of modification groups, numbers and positions not only affect the color and stability of anthocyanins, but also largely expand their species. In recent years, enzymes involved in anthocyanin modifications have been widely reported in different species. Based on the sequenced genome, short life span and distinct anthocyanin composition, Arabidopsis thaliana has become an ideal material to study the anthocyanin modification pathway. This review summarized the progress made towards anthocyanin modification pathways in Arabidopsis.%花青素属于类黄酮化合物,赋予了植物从红色、蓝色到紫色的多种颜色,在帮助植物吸引昆虫为其传粉和传播种子等方面发挥着重要功能.现有研究表明花青素的呈色和稳定性与其修饰基团类别、数目和位置等要素密切相关.近年来,在不同物种中发现了参与花青素修饰的各种酶.模式植物拟南芥因其基因组信息清楚,生长周期短和花青素组成明确等特点成了研究花青素修饰途径的理想材料.本文主要综述了拟南芥中花青素合成后的修饰过程及其产物多样性.

  3. Arabidopsis TT19 Functions as a Carrier to Transport Anthocyanin from the Cytosol to Tonoplasts

    Yi Sun; Hong Li; Ji-Rong Huang

    2012-01-01

    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.

  4. Impact of pectin type on the storage stability of black currant (Ribes nigrum L.) anthocyanins in pectic model solutions.

    Buchweitz, M; Speth, M; Kammerer, D R; Carle, R

    2013-08-15

    The effects of different pectins on the stabilisation of black currant anthocyanins in viscous model solutions at pH 3.0 were investigated. For this purpose, low esterified amidated (AM), low (LM) and high (HM) methoxylated citrus and apple pectins and a sugar beet pectin were added to a purified anthocyanin extract (ACN-E) and to an extract containing anthocyanins and non-anthocyanin phenolics (PP-E). Model systems were stored at 20±0.5°C in the dark. Anthocyanin contents were monitored by HPLC analysis over a period of 18 weeks, and half-life and destruction values were calculated. In all pectic model solutions anthocyanin stability was significantly improved compared to stability of the extracts without added pectins (blank). Best stabilisation was obtained with AM pectin, followed by LM and HM pectins. In model systems containing citrus pectins, anthocyanin stabilisation was better compared to that of apple pectins having similar degrees of esterification and amidation, respectively. This was primarily due to the strong interaction of delphinidin glycosides with the citrus pectins, whereas stabilisation of cyanidin derivatives was less important. Sugar beet pectin improved anthocyanin stability only to a limited extent. In the presence of non-anthocyanin phenolics (PP-E) the impact of the pectin source was even more pronounced than the effect of the pectin type. Addition of citrate to pectic systems accelerated anthocyanin decay. Stabilising effects of pectins were hardly noticeable when evaluating total phenolic content (TPC, Folin-Ciocalteu) and antioxidant capacity during storage. Highest TPC, TEAC- and FRAP values were observed in systems containing citrus pectin, which was in contrast to sugar beet pectin, where values fell below those of the blank after storage. PMID:23561223

  5. Plant Cytosolic Acyl-CoA-Binding Proteins.

    Ye, Zi-Wei; Chye, Mee-Len

    2016-01-01

    A gene family encoding six members of acyl-CoA-binding proteins (ACBP) exists in Arabidopsis and they are designated as AtACBP1-AtACBP6. They have been observed to play pivotal roles in plant lipid metabolism, consistent to the abilities of recombinant AtACBP in binding different medium- and long-chain acyl-CoA esters in vitro. While AtACBP1 and AtACBP2 are membrane-associated proteins with ankyrin repeats and AtACBP3 contains a signaling peptide for targeting to the apoplast, AtACBP4, AtACBP5 and AtACBP6 represent the cytosolic forms in the AtACBP family. They were verified to be subcellularly localized in the cytosol using diverse experimental methods, including cell fractionation followed by western blot analysis, immunoelectron microscopy and confocal laser-scanning microscopy using autofluorescence-tagged fusions. AtACBP4 (73.2 kDa) and AtACBP5 (70.1 kDa) are the largest, while AtACBP6 (10.4 kDa) is the smallest. Their binding affinities to oleoyl-CoA esters suggested that they can potentially transfer oleoyl-CoA esters from the plastids to the endoplasmic reticulum, facilitating the subsequent biosynthesis of non-plastidial membrane lipids in Arabidopsis. Recent studies on ACBP, extended from a dicot (Arabidopsis) to a monocot, revealed that six ACBP are also encoded in rice (Oryza sativa). Interestingly, three small rice ACBP (OsACBP1, OsACBP2 and OsACBP3) are present in the cytosol in comparison to one (AtACBP6) in Arabidopsis. In this review, the combinatory and distinct roles of the cytosolic AtACBP are discussed, including their functions in pollen and seed development, light-dependent regulation and substrate affinities to acyl-CoA esters. PMID:26662549

  6. Induction of anthocyanins accumulation by methyl jasmonate in shoots of Crassula multicava Lam.

    Marian Saniewski; Marcin Harbowicz; Jerzy Puchalski

    2012-01-01

    In Crassula multicava Lam. anthocyanins are formed naturally mostly in the stem near nodes and only traces in other parts of internodes. Methyl jasmonate (JA-Me) applied in lanolin paste at concentrations of 0.05, 0.1, 0.5 and 1.0% on the middle part of internodes greatly stimulated anthocyanins accumulation in the internodes and in the nodes of Crassula multicava. The stimulatory effect was higher in younger tissues of the Crassula multicava stem than in older ones, and depends on the u...

  7. Anthocyanin concentration of "Assaria" pomegranate fruits during different cold storage conditions

    Graça Miguel; Catarina Fontes; Dulce Antunes; Alcinda Neves; Denise Martins

    2004-01-01

    The concentration of anthocyanins in fruits of "Assaria" pomegranate, a sweet Portuguese cultivar typically grown in Algarve (south Portugal), was monitored during storage under different conditions. The fruits were exposed to cold storage (5 degrees C) after the following treatments: spraying with wax; spraying with 1.5% CaCl2; spraying with wax and 1.5% CaCl2; covering boxes with 25 mu c thickness low-density polyethylene film. Untreated fruits were used as a control. The anthocyanin levels...

  8. Transcriptome Profiling of Light-Regulated Anthocyanin Biosynthesis in the Pericarp of Litchi

    Zhang, Hong-Na; Li, Wei-Cai; Wang, Hui-Cong; Shi, Sheng-You; Shu, Bo; Liu, Li-Qin; Wei, Yong-Zan; Xie, Jiang-Hui

    2016-01-01

    Light is a key environmental factor that affects anthocyanin biosynthesis. To enhance our understanding of the mechanisms involved in light-regulated anthocyanin biosynthesis in the pericarp of litchi, we performed transcriptomic analyses on the basis of Illumina sequencing. Fruit clusters were bagged with double-layer Kraft paper bags at 42 days after anthesis. The bags were removed after 2 weeks. Under light conditions, anthocyanins accumulated rapidly in the pericarp. RNA sequences were de novo assembled into 75,935 unigenes with an average length of 913 bp. Approximately 74.5% of unigenes (56,601) were annotated against four public protein databases. A total of 16,622 unigenes that significantly differed in terms of abundance were identified. These unigenes are implicated in light signal perception and transduction, flavonoid biosynthesis, carotenoid biosynthesis, plant hormone signal transduction, and photosynthesis. In photoreceptors, the expression levels of UV RESISTANCE LOCUS 8 (UVR8), Phototropin 2 (PHOT2), Phytochrome B (PHYB), and Phytochrome C (PHYC) increased significantly when the fruits were exposed to light. This result indicated that they likely play important roles in anthocyanin biosynthesis regulation. After analyzed digital gene expression (DGE), we found that the light signal transduction elements of COP1 and COP10 might be responsible for anthocyanin biosynthesis regulation. After the bags were removed, nearly all structural and regulatory genes, such as UDP-glucose: flavonoid-3-O-glucosyltransferase (UFGT), MYB, basic helix-loop-helix (bHLH), and WD40, involved in the anthocyanin biosynthetic pathway were upregulated. In addition to MYB-bHLH-WD40 transcription complex, ELONGATED HYPOCOTYL (HY5), NAM/ATAF/CUC (NAC), homeodomain leucine zipper proteins (ATHBs), and FAR-RED ELONGATED HYPOCOTYL (FHY) possibly participate in light-induced responses. On the basis of DGEs and qRT-PCR validation, we observed a light-induced anthocyanin biosynthesis

  9. Anthocyanin Characterization of Pilot Plant Water Extracts of Delonix regia Flowers

    Emile M. Gaydou

    2008-06-01

    Full Text Available Following the development of new applications of pilot plant scale extraction and formulation processes for natural active bioproducts obtained from various underutilized tropical plants and herbs, we have manufactured water-extracts from Delonix regia flowers, grown in Ivory Coast. These extracts, which contain polyphenols, are traditionally home made and used as healthy bioproducts. They are reddish-coloured due to the presence of anthocyanins. The three major anthocyanins in these extracts have been characterized. The molecular structures were confirmed by LC-SM analysis. Amongst them, two are described for the first time in Delonix regia.

  10. Anthocyanin characterization of pilot plant water extracts of Delonix regia flowers.

    Adje, Felix; Lozano, Yves F; Meudec, Emmanuelle; Lozano, Paul; Adima, Augustin; N'zi, Georges Agbo; Gaydou, Emile M

    2008-01-01

    Following the development of new applications of pilot plant scale extraction and formulation processes for natural active bioproducts obtained from various underutilized tropical plants and herbs, we have manufactured water-extracts from Delonix regia flowers, grown in Ivory Coast. These extracts, which contain polyphenols, are traditionally home made and used as healthy bioproducts. They are reddish-coloured due to the presence of anthocyanins. The three major anthocyanins in these extracts have been characterized. The molecular structures were confirmed by LC-SM analysis. Amongst them, two are described for the first time in Delonix regia. PMID:18596650

  11. Tissue- Specific Expression Analysis of Anthocyanin Biosynthetic Genes in White- and Red-Fleshed Grape Cultivars

    Sha Xie; Changzheng Song; Xingjie Wang; Meiying Liu; Zhenwen Zhang; Zhumei Xi

    2015-01-01

    Yan73, a teinturier (dyer) grape variety in China, is one of the few Vitis vinifera cultivars with red-coloured berry flesh. To examine the tissue-specific expression of genes associated with berry colour in Yan73, we analysed the differential accumulation of anthocyanins in the skin and flesh tissues of two red-skinned grape varieties with either red (Yan73) or white flesh (Muscat Hamburg) based on HPLC-MS analysis, as well as the differential expression of 18 anthocyanin biosynthesis genes ...

  12. Subspecialization of R2R3-MYB Repressors for Anthocyanin and Proanthocyanidin Regulation in Forage Legumes

    Albert, Nick W.

    2015-01-01

    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 a...

  13. Efficient free fatty acid production in Escherichia coli using plant acyl-ACP thioesterases.

    Zhang, Xiujun; Li, Mai; Agrawal, Arpita; San, Ka-Yiu

    2011-11-01

    Microbial biosynthesis of fatty acid-like chemicals from renewable carbon sources has attracted significant attention in recent years. Free fatty acids can be used as precursors for the production of fuels or chemicals. Free fatty acids can be produced by introducing an acyl-acyl carrier protein thioesterase gene into Escherichia coli. The presence of the acyl-ACP thioesterase will break the fatty acid elongation cycle and release free fatty acid. Depending on their sequence similarity and substrate specificity, class FatA thioesterase is active on unsaturated acyl-ACPs and class FatB prefers saturated acyl group. Different acyl-ACP thioesterases have different degrees of chain length specificity. Although some of these enzymes have been characterized from a number of sources, information on their ability to produce free fatty acid in microbial cells has not been extensively examined until recently. In this study, we examined the effect of the overexpression of acyl-ACP thioesterase genes from Diploknema butyracea, Gossypium hirsutum, Ricinus communis and Jatropha curcas on free fatty acid production. In particular, we are interested in studying the effect of different acyl-ACP thioesterase on the quantities and compositions of free fatty acid produced by an E. coli strain ML103 carrying these constructs. It is shown that the accumulation of free fatty acid depends on the acyl-ACP thioesterase used. The strain carrying the acyl-ACP thioesterase gene from D. butyracea produced approximately 0.2g/L of free fatty acid while the strains carrying the acyl-ACP thioesterase genes from R. communis and J. curcas produced the most free fatty acid at a high level of more than 2.0 g/L at 48 h. These two strains accumulated three major straight chain free fatty acids, C14, C16:1 and C16 at levels about 40%, 35% and 20%, respectively. PMID:22001432

  14. Microbial transglutaminase displays broad acyl-acceptor substrate specificity

    T. Gundersen, Maria; Keillor, Jeffrey W.; Pelletier, Joelle N.

    2013-01-01

    The great importance of amide bonds in industrial synthesis has encouraged the search for efficient catalysts of amide bond formation. Microbial transglutaminase (MTG) is heavily utilized in crosslinking proteins in the food and textile industries, where the side chain of a glutamine reacts with....... Importantly, very small amines carrying either the electron-rich azide or the alkyne groups required for click chemistry were highly reactive as acyl-acceptor substrates, providing a robust route to minimally modified, “clickable” peptides. These results demonstrate that MTG is tolerant to a variety of...

  15. Acylated flavonol glycosides from the flower of Inula britannica.

    Park, E J; Kim, Y; Kim, J

    2000-01-01

    Three new acylated flavonol glycosides, patuletin 7-O-(6' '-isobutyryl)glucoside (1), patuletin 7-O-[6' '-(2-methylbutyryl)]glucoside (2), and patuletin 7-O-(6' '-isovaleryl)glucoside (3), were isolated from the n-BuOH extract of Inula britannica flowers by bioassay-guided fractionation, together with other known flavonoids. The structures were elucidated by 1D and 2D NMR, FABMS, and other spectral analyses. The eight flavonoids, including new compounds (1-3), patulitrin (7), nepitrin (8), axillarin (10), patuletin (11), and luteolin (12), showed profound antioxidant activity in DPPH assay and cytochrome-c reduction assay using HL-60 cell culture system. PMID:10650074

  16. Evolution of the acyl-CoA binding protein (ACBP)

    Burton, Mark; Rose, Timothy M; Faergeman, Nils J;

    2005-01-01

    -CoA pool size, donation of acyl-CoA esters for beta-oxidation, vesicular trafficking, complex lipid synthesis and gene regulation. In the present study, we delineate the evolutionary history of ACBP to get a complete picture of its evolution and distribution among species. ACBP homologues were identified...... duplication and/or retrotransposition events. The ACBP protein is highly conserved across phylums, and the majority of ACBP genes are subjected to strong purifying selection. Experimental evidence indicates that the function of ACBP has been conserved from yeast to humans and that the multiple lineage...

  17. Synthesis of photoactivatable azido-acyl caged oxazine fluorophores for live-cell imaging.

    Anzalone, Andrew V; Chen, Zhixing; Cornish, Virginia W

    2016-07-19

    We report the design and synthesis of a photoactivatable azido-acyl oxazine fluorophore. Photoactivation is achieved cleanly and rapidly with UV light, producing a single fluorescent oxazine photoproduct. We demonstrate the utility of azido-acyl caged oxazines for protein specific labeling in living mammalian cells using the TMP-tag technology. PMID:27377037

  18. 1,5-Anhydro-D-fructose: regioselective acylation with fatty acids

    Lundt, Inge; Andersen, Søren Møller; Marcussen, Jan; Yu, Shukun

    Regioselective acylation of 1,5-anhydro-D-fructose was performed with dodecanoic acid to give 1,5-anhydro-6-O-dodecanoyl-D-fructose, chemically in 50% yield and enzymatically in quantitative yield. Quantitative conversions were also obtained using hexadecanoic and octadecanoic acids as acyl donors...

  19. Influence of Lipid A Acylation Pattern on Membrane Permeability and Innate Immune Stimulation

    Robert K. Ernst

    2013-08-01

    Full Text Available Lipid A, the hydrophobic anchor of lipopolysaccharide (LPS, is an essential component in the outer membrane of Gram-negative bacteria. It can stimulate the innate immune system via Toll-like receptor 4/myeloid differentiation factor 2 (TLR4/MD2, leading to the release of inflammatory cytokines. In this study, six Escherichia coli strains which can produce lipid A with different acylation patterns were constructed; the influence of lipid A acylation pattern on the membrane permeability and innate immune stimulation has been systematically investigated. The lipid A species were isolated and identified by matrix assisted laser ionization desorption-time of flight/tandem mass spectrometry. N-Phenyl naphthylamine uptake assay and antibiotic susceptibility test showed that membrane permeability of these strains were different. The lower the number of acyl chains in lipid A, the stronger the membrane permeability. LPS purified from these strains were used to stimulate human or mouse macrophage cells, and different levels of cytokines were induced. Compared with wild type hexa-acylated LPS, penta-acylated, tetra-acylated and tri-acylated LPS induced lower levels of cytokines. These results suggest that the lipid A acylation pattern influences both the bacterial membrane permeability and innate immune stimulation. The results would be useful for redesigning the bacterial membrane structure and for developing lipid A vaccine adjuvant.

  20. Acyl-CoA binding proteins; structural and functional conservation over 2000 MYA

    Faergeman, Nils J; Wadum, Majken; Feddersen, Søren;

    2007-01-01

    -CoA binding protein, ACBP, has been proposed to play a pivotal role in the intracellular trafficking and utilization of long-chain fatty acyl-CoA esters. Depletion of acyl-CoA binding protein in yeast results in aberrant organelle morphology incl. fragmented vacuoles, multi-layered plasma membranes and...

  1. A Stereoelectronic Basis for the Kinetic Resolution of N-Heterocycles with Chiral Acylating Reagents

    Hsieh, Sheng-Ying; Wanner, Benedikt; Wheeler, Philip; Beauchemin, André M.; Rovis, Tomislav; Bode, Jeffrey W.

    2014-01-01

    The kinetic resolution of N-heterocycles with chiral acylating agents reveals a previously unrecognized stereoelectronic effect in amine acylation. Combined with a new achiral hydroxamate, this effect makes possible the resolution of various N-heterocycles using easily prepared reagents. A transition state model to rationalize the stereochemical outcome of this kinetic resolution is also proposed.

  2. Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl β-C-Glycosides.

    Guisot, Nicolas E S; Ella Obame, Idriss; Ireddy, Prathap; Nourry, Arnaud; Saluzzo, Christine; Dujardin, Gilles; Dubreuil, Didier; Pipelier, Muriel; Guillarme, Stéphane

    2016-03-18

    A new strategy for the synthesis of acyl β-C-glycosides is described. The reactivity of glyconitriles toward organometallic reagents such as organomagnesium or organolithium derivatives was studied, affording acyl β-C-glycosides in moderate to good yields. In this study, glycal formation was efficiently prevented by deprotonating the hydroxyl group in position 2 of the glyconitriles during the process. PMID:26926714

  3. Suppression of acyl migration in enzymatic production of structured lipids through temperature programming

    Yang, Tiankui; Fruekilde, Maj-Britt; Xu, Xuebing

    2005-01-01

    Acyl migration in the glycerol backbone often leads to the increase of by-products in the enzymatic production of specific structured lipids. Acyl migration is a thermodynamic process and is very difficult to stop fully in actual reactions. The objective of this study was to investigate the feasi......Acyl migration in the glycerol backbone often leads to the increase of by-products in the enzymatic production of specific structured lipids. Acyl migration is a thermodynamic process and is very difficult to stop fully in actual reactions. The objective of this study was to investigate...... the feasibility of suppressing acyl migration by a programmed change of reaction temperature without loss of reaction yield. The model reactions were the acidolysis of tripalmitin with conjugated linoleic acid (CLA) or with caprylic acid (CA) targeted for human milk fat substitutes. Acyl migration...... was considerably inhibited in the temperature-programmed acidolysis of PPP with CLA or CA, with only slight reduction of acyl incorporation, the reaction leading to the required products. Acyl migration was reduced by 29% (35 h) and 45% (48 h), respectively, in the acidolysis of PPP with CLA under solvent...

  4. Acylation of aromatic alcohols and phenols over InCl3/montmorillonite K-10 catalysts

    Vasant R Choudhary; Kailash Y Patil; Suman K Jana

    2004-03-01

    Montmorillonite K-10 clay supported InCl3 is a highly active catalyst for the acylation of aromatic alcohols and phenols with different acyl chlorides. This catalyst can be reused in reactions a number of times without very significant loss of catalytic activity.

  5. Accumulation of N-acyl-ethanolamine phospholipids in rat brains during post-decapitative ischemia

    Moesgaard, B.; Hansen, Harald S.; Jaroszewski, J.W.

    1999-01-01

    Phosphorus-31 nuclear magnetic resonance (P NMR) spectroscopy has been used to study accumulation of N-acyl-ethanolamine phospholipids in rat brains during post-decapitative ischemia. Lipids were extracted from rat brain homogenates and the extracts were thoroughly washed with aq. potassium...... NMR spectra at 0.18 and 0.22 ppm (relative to the chemical shift of 1,2-diacyl-sn-glycero-3-phosphocholine (PCD(DIACYL)) at -0.84 ppm). These signals were identified as originating from 1,2-diacyl- sn-glycero-3-phospho-(N-acyl)-ethanolamine (NAPED(DIACYL)) and 1-(1'- alkenyl)-2-acyl-sn-glycero-3......-phospho(N-acyl)-ethanolamine (NAPE(PLAS)), respectively, by spiking with authentic materials. Additionally, the identification was verified by thin-layer chromatography, which also showed the accumulation of N-acyl-ethanolamine phospholipids. The use of K-EDTA instead of the commonly used Cs-EDTA in the...

  6. Acylation of salmon calcitonin modulates in vitro intestinal peptide flux through membrane permeability enhancement

    Trier, Sofie; Linderoth, Lars; Bjerregaard, Simon;

    2015-01-01

    Acylation of peptide drugs with fatty acid chains has proven beneficial for prolonging systemic circulation, as well as increasing enzymatic stability and interactions with lipid cell membranes. Thus, acylation offers several potential benefits for oral delivery of therapeutic peptides, and we...... its influence on intestinal cell translocation and membrane interaction. We find that acylation drastically increases in vitro intestinal peptide flux and confers a transient permeability enhancing effect on the cell layer. The analogues permeabilize model lipid membranes, indicating that the effect...... is due to a solubilization of the cell membrane, similar to transcellular oral permeation enhancers. The effect is dependent on pH, with larger effect at lower pH, and is impacted by acylation chain length and position. Compared to the unacylated peptide backbone, N-terminal acylation with a short...

  7. Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments

    Annamaria Deagostino

    2013-01-01

    Full Text Available Since the first report and due to its handiness and wide scope, the Suzuki-Miyaura (SM cross coupling reaction has become a routine methodology in many laboratories worldwide. With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so far less exploited as a tool to introduce an acyl function into a specific substrate. In this review, the various approaches found in the literature will be considered, starting from the direct SM acylative coupling to the recent developments of cross coupling between boronates and acyl chlorides or anhydrides. Special attention will be dedicated to the use of masked acyl boronates, alkoxy styryl and alkoxy dienyl boronates as coupling partners. A final section will be then focused on the acyl SM reaction as key synthetic step in the framework of natural products synthesis.

  8. Impact of cluster thinning on transcriptional regulation of anthocyanin biosynthesis-related genes in 'Summer Black' grapes.

    Xi, Xiaojun; Zha, Qian; Jiang, Aili; Tian, Yihua

    2016-07-01

    Cluster thinning is an agronomic practice that strongly affects anthocyanin biosynthesis in the skin of grape berries. However, the impact of cluster thinning on anthocyanin biosynthesis has not been fully elucidated at the molecular level. Here, we investigated its effects on the berry quality, the biosynthesis of anthocyanins, and the expression levels of related genes from the onset of véraison to harvest in 'Summer Black' grapes. It was observed that the total soluble solid and anthocyanin content in berry skin significantly increased under cluster thinning, whereas the berry weight and titratable acidity showed no differences from the beginning of véraison to harvest. The expression level of most anthocyanin biosynthesis-related genes was significantly up-regulated by cluster thinning from the beginning of véraison and was higher at its end compared to the control. Up-regulation of flavonoid 3',5'-hydroxylase (F3'5'H) and O-methyltransferase (OMT) expression, and down-regulation of flavonoid 3'-hydroxylase (F3'H) expression were observed, which might be the cause of shift in the anthocyanin profile. These findings provide insights into the molecular basis of the relationship between cluster thinning and anthocyanin biosynthesis in the grape berry skin. PMID:27035257

  9. Melatonin Improved Anthocyanin Accumulation by Regulating Gene Expressions and Resulted in High Reactive Oxygen Species Scavenging Capacity in Cabbage.

    Zhang, Na; Sun, Qianqian; Li, Hongfei; Li, Xingsheng; Cao, Yunyun; Zhang, Haijun; Li, Shuangtao; Zhang, Lei; Qi, Yan; Ren, Shuxin; Zhao, Bing; Guo, Yang-Dong

    2016-01-01

    In this work, we found, that exogenous melatonin pretreatment improved anthocyanin accumulation (1- to 2-fold) in cabbage. To verify the relationship with melatonin and anthocyanin, an Arabidopsis mutant, snat, which expresses a defective form of the melatonin biosynthesis enzyme SNAT (Serotonin N-acetyl transferase), was employed. Under cold conditions, the foliage of wild-type Arabidopsis exhibited a deeper red color than the snat mutant. This finding further proved, that exogenous melatonin treatment was able to affect anthocyanin accumulation. To gain a better understanding of how exogenous melatonin upregulates anthocyanin, we measured gene expression in cabbage samples treated with melatonin and untreated controls. We found that the transcript levels of anthocyanin biosynthetic genes were upregulated by melatonin treatment. Moreover, melatonin treatment increased the expression levels of the transcription factors MYB, bHLH, and WD40, which constitute the transcriptional activation complex responsible for coordinative regulation of anthocyanin biosynthetic genes. We found, that free radical generation was downregulated, whereas the osmotic adjustment and antioxidant capacities were upregulated in exogenous melatonin-treated cabbage plants. We concluded, that melatonin increases anthocyanin production and benefits cabbage growth. PMID:27047496

  10. Relationships between acylated ghrelin with growth hormone, insulin resistance, lipid profile, and cardio respiratory function in lean and obese men

    Hasan Matin Homaee

    2011-01-01

    Conclusions: Obese and lean inactive young men had different levels of acylated ghrelin, GH, insulin, insulin resistance index, cardiorespiratory function and body fat percent. Body fat percent, insulin, and GH levels appear to be best determinant factors of acylated ghrelin levels. Also, in both obese and lean young men, higher levels of cardiovascular function were associated with higher levels of acylated ghrelin.

  11. Substantial species differences in relation to formation and degradation of N-acyl-ethanolamine phospholipids in heart tissue

    Moesgaard, B.; Petersen, G.; Hansen, Harald S.;

    2002-01-01

    The formation of N-acyl-ethanolamines (NAEs), including the cannabinoid receptor ligand anandamide, and their precursors N-acyl-ethanolamine phospholipids (NAPEs) are catalyzed by NAPE-hydrolyzing phospholipase D (NAPE-PLD) and N-acyl-transferase, respectively. NAPE and NAE are suggested to have...

  12. Stilbenes and anthocyanins reduce stress signaling in BV-2 mouse microglia

    Blueberries contain an array of phytochemicals that may decrease both inflammatory and oxidative stress. We determined if pterostilbene, resveratrol, and two anthocyanins commonly found in blueberries, delphinidin-3-O-glucoside and malvidin-3-O-glucoside, would be efficacious in protecting microglia...

  13. Red Chicory (Cichorium intybus L. cultivar as a Potential Source of Antioxidant Anthocyanins for Intestinal Health

    Laura D'evoli

    2013-01-01

    Full Text Available Fruit- and vegetable-derived foods have become a very significant source of nutraceutical phytochemicals. Among vegetables, red chicory (Cichorium Intybus L. cultivar has gained attention for its content of phenolic compounds, such as the anthocyanins. In this study, we evaluated the nutraceutical effects, in terms of antioxidant, cytoprotective, and antiproliferative activities, of extracts of the whole leaf or only the red part of the leaf of Treviso red chicory (a typical Italian red leafy plant in various intestinal models, such as Caco-2 cells, differentiated in normal intestinal epithelia and undifferentiated Caco-2 cells. The results show that the whole leaf of red chicory can represent a good source of phytochemicals in terms of total phenolics and anthocyanins as well as the ability of these phytochemicals to exert antioxidant and cytoprotective effects in differentiated Caco-2 cells and antiproliferative effects in undifferentiated Caco-2 cells. Interestingly, compared to red chicory whole leaf extracts, the red part of leaf extracts had a significantly higher content of both total phenolics and anthocyanins. The same extracts effectively corresponded to an increase of antioxidant, cytoprotective, and antiproliferative activities. Taken together, these findings suggest that the red part of the leaf of Treviso red chicory with a high content of antioxidant anthocyanins could be interesting for development of new food supplements to improve intestinal health.

  14. Preheated milk proteins improve the stability of grape skin anthocyanins extracts.

    He, Zhiyong; Xu, Mingzhu; Zeng, Maomao; Qin, Fang; Chen, Jie

    2016-11-01

    The effects of casein and whey proteins, preheated at 40-100°C and 45-60°C for 15min, respectively, on color loss and anthocyanins degradation in grape skin anthocyanins extracts (GSAE) at pH 3.2 and 6.3 were evaluated. Preheating milk proteins effectively improved their protective effects against color loss and anthocyanins degradation in GSAE solutions during thermal treatment (at 80°C for 2h), H2O2 oxidation (0.005% H2O2 for 1h) and illumination (at 5000lx for 5 d). Whey proteins and casein, preheated at 50°C and 60°C for 15min, respectively, demonstrated the optimal protective effects. However, preheated whey proteins had a better protective effect on the thermal, oxidation and photo stability of GSAE, decreasing the thermal, oxidative and photo degradation of anthocyanins in GSAE 71.59%, 32.22% and 56.92% at pH 3.2 and 54.91%, 22.89% and 46.68% at pH 6.3, respectively. PMID:27211641

  15. The influence of clay surface modification with berberine on the sorption of anthocyanins

    Chulkov, A. N.; Deineka, V. I.; Tikhova, A. A.; Vesentzev, A. I.; Deineka, L. A.

    2012-03-01

    The influence of preliminary sorption of berberine on the sorption of anthocyanins by bentonite clay was studied. The cation exchange sorption mechanism was found to be replaced by hydrophobic sorption of these compounds after clay modification with berberine. The enthalpy of sorption along the initial isotherm part changed from endothermic to exothermic.

  16. Variability in anthocyanin content among Abutilon theophrasti, and Urena lobata genetic resources .

    Plants contain bioactive phytochemicals and nutraceuticals to be utilized in the pharmaceutical and nutraceutical markets. Sixty-two accessions of Abutilon theophrasti, Basella alba, and Urena lobata are conserved at the USDA, ARS, Plant Genetic Resources Conservation Unit, Griffin, GA. Anthocyanins...

  17. Genetic engineering of novel bluer-colored chrysanthemums produced by accumulation of delphinidin-based anthocyanins.

    Noda, Naonobu; Aida, Ryutaro; Kishimoto, Sanae; Ishiguro, Kanako; Fukuchi-Mizutani, Masako; Tanaka, Yoshikazu; Ohmiya, Akemi

    2013-10-01

    Chrysanthemums (Chrysanthemum morifolium Ramat.) have no purple-, violet- or blue-flowered cultivars because they lack delphinidin-based anthocyanins. This deficiency is due to the absence of the flavonoid 3',5'-hydroxylase gene (F3'5'H), which encodes the key enzyme for delphinidin biosynthesis. In F3'5'H-transformed chrysanthemums, unpredictable and unstable expression levels have hampered successful production of delphinidin and reduced desired changes in flower color. With the aim of achieving delphinidin production in chrysanthemum petals, we found that anthocyanin biosynthetic gene promoters combined with a translational enhancer increased expression of some F3'5'H genes and accompanying delphinidin-based anthocyanin accumulation in transgenic chrysanthemums. Dramatic accumulation of delphinidin (up to 95%) was achieved by simple overexpression of Campanula F3'5'H controlled by a petal-specific flavanone 3-hydroxylase promoter from chrysanthemum combined with the 5'-untranslated region of the alcohol dehydrogenase gene as a translational enhancer. The flower colors of transgenic lines producing delphinidin-based anthocyanins changed from a red-purple to a purple-violet hue in the Royal Horticultural Society Colour Charts. This result represents a promising step toward molecular breeding of blue chrysanthemums. PMID:23926063

  18. Dyeing of Silk with Anthocyanins Dyes Extract from Liriope platyphylla Fruits

    Huayin Wang

    2014-01-01

    Full Text Available A new source of natural anthocyanins dyes, from Liriope platyphylla fruit, is proposed. This paper analyzes the dye extracts, the primary color components of the extracts, the color features of the extracts under different pH conditions, and their application in silk dyeing. The research shows that, nine anthocyanins are found in  L. platyphylla fruits by analyzing the results of the HPLC/DAD, MS, and MS/MS spectra. The five major anthocyanins related to delphinidin, petunidin, and malvidin derivatives take up 91.72% of total anthocyanin contents. The color of the solution is red under acidic condition (pH < 3.0 and stays in yellow under alkaline condition with pH values above 7.0. The dye extracts applied to silk fabric with mordant free dyeing show different color under different pH conditions, changing between purple, blue, green, and yellow. However, the dyed colors is light and the dyeing rate is low. Metal mordant such as Sn in chelation enhances the dye depth and improves the fastness of the dyed silk fabrics, especially in silk fabrics dyed by premordanting and metamordanting.

  19. Transgene-based anthocyanin hyper-pigmentation as a visual reporter of gene silencing in plants

    “Co-suppression” associated loss of flower pigmentation in transgenic petunia plants was one of the first clear indicators of the natural process of RNA-associated gene silencing in plants. We have been exploring the use of genetically engineered anthocyanin over-production in vegetative tissues as...

  20. Sour Cherry (Prunus cerasus L.) Anthocyanins: effects of juice processing on phenolic compounds and bioavailability

    Toydemir, G.; Boyacioglu, D.; Beekwilder, M.J.; Vos, de R.C.H.; Hall, R.D.; Capanoglu, E.

    2014-01-01

    Sour cherry (Prunus cerasus L.), has gained growing interest in recent years due to the envisaged health benefits associated with a regular intake of anthocyanins and related polyphenolic compounds. Turkish sour cherries are widely consumed as processed products and are renowned for their high juice

  1. Effect on in vitro starch digestibility of Mexican blue maize anthocyanins.

    Camelo-Méndez, Gustavo A; Agama-Acevedo, Edith; Sanchez-Rivera, Mirna M; Bello-Pérez, Luis A

    2016-11-15

    The purpose of this study was to evaluate the effect of blue maize extracts obtained by acid-methanol treatment on the nutritional in vitro starch fractions such as: rapidly digestive starch (RDS), slowly digestive starch (SDS) and resistant starch (RS) of native and gelatinized commercial maize starch. Chromatographic analysis (HPLC-DAD/ESI-MS) of blue maize extracts showed the presence of seven anthocyanins, where cyanidin-3-(6″-malonylglucoside) was the main. Blue maize extracts modified nutritional in vitro starch fractions (decrease of RDS) while RS content increased (1.17 and 2.02 times for native and gelatinized commercial maize starch, respectively) when anthocyanins extracts were added to starch up to 75% (starch weight). This preliminary observation provides the basis for further suitability evaluation of blue maize extract as natural starch-modifier by the possible anthocyanins-starch interaction. Anthocyanin extracts can be a suitable to produce functional foods with higher RS content with potential human health benefits. PMID:27283633

  2. Viscous Food Matrix Influences Absorption and Excretion but Not Metabolism of Blackcurrant Anthocyanins in Rats

    Walton, M.C.; Hendriks, W.H.; Broomfield, A.M.; McGhie, T.K.

    2009-01-01

    The aim of the present study was to investigate the effect of a simultaneous intake of food and anthocyanins (ACNs) on ACN absorption, metabolism, and excretion. Blackcurrant ACNs (BcACNs) were dissolved in water with or without the addition of oatmeal and orally administered to rats, providing appr

  3. Microencapsulation optimization of natural anthocyanins with maltodextrin, gum Arabic and gelatin.

    Akhavan Mahdavi, Sahar; Jafari, Seid Mahdi; Assadpoor, Elham; Dehnad, Danial

    2016-04-01

    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%. PMID:26772915

  4. Combining ability of sweetpotato germplasm for yield, dry matter content, and anthocyanin production

    Interest in the potential of sweetpotato (Ipomoea batatas) for the production of industrial products is increasing. As part of an effort to evaluate the potential of sweetpotatoes for starch and anthocyanin production in the southeastern United States, a 5 x 5 North Carolina mating design II (NCII m...

  5. Natural variation in petal color in Lycoris longituba revealed by anthocyanin components.

    Qiuling He

    Full Text Available Lycoris longituba is one of the species belonging to the Amaryllidaceae family. Despite its limited distribution, endemic to central eastern China, this species displays an exceptionally wide diversity of flower colors from purple, red, orange, to yellow, in nature. We study the natural variation of floral color in L. longituba by testing the components of water-soluble vacuolar pigments--anthocyanins--in its petals using high-performance liquid chromatography coupled with photodiode array detection and electrospray ionization mass spectrometry. Four anthocyanins were identified, cyanidin-3-sophoroside (Cy3So, cyanidin-3-xylosylglucoside (Cy3XyGlc, cyanidin-3-sambubioside (Cy3Sa, and pelargonidin-3-xylosylglucoside (Pg3XyGlc, which occur at various amounts in L. longituba petals of different colors. A multivariate analysis was used to explore the relationship between pigments and flower color. Anthocyanins have been thought to play a major role in acting as a UV screen that protects the plant's DNA from sunlight damage and attracting insects for the purpose of pollination. Thus, knowledge about the content and type of anthocyanins determining the petal coloration of Lycoris longituba will help to study the adaptive evolution of flowers and provide useful information for the ornamental breeding of this species.

  6. Anthocyanin, phenolics and antioxidant activity changes in purple waxy corn as affected by traditional cooking

    Antioxidant components, including anthocyanins and phenolic compounds, antioxidant activity, and their changes during traditional cooking of fresh purple waxy corn were investigated. As compared to the raw corn, thermal treatment caused significant (p < 0.05) decreases in each antioxidant compound a...

  7. Inheritance of anthocyanin content in the ripe berries of a tetraploid × diploid grape cross population

    Variation patterns and inheritance of anthocyanin content in the ripe berries of a tetraploid × diploid table grape cross population were investigated in two successive years. The population segregated for three different ploidy levels: dipolids, triploids, and tetraploids. A total of 28 different a...

  8. Chromaticity and color saturation of ultraviolet irradiated poly(vinyl alcohol)-anthocyanin coatings

    Mat Nor, N. A.; Aziz, N.; Mohd-Adnan, A. F.; Taha, R. M.; Arof, A. K.

    2016-06-01

    The purpose of this paper is to evaluate the chromaticity and color saturation of anthocyanin extraction from fruit pericarps of Ixora siamensis in a poly(vinyl alcohol) (PVA) matrix. The colored PVA matrix was exposed to UV-B irradiation for 93 days at UV intensity of 17.55 lux. Anthocyanin colorant has been extracted using methanol acidified with 0.5% trifluoroacetic acid (TFA). Different concentrations of ferulic acid (FA) (0, 1, 2, 3, 4 and 5 wt.%) have been added to the anthocyanin extractions before mixing with PVA to form a coating system. The PVA-anthocyanin-FA mixtures have been coated on glass slides and kept overnight in the dark for curing before exposure to UV-B irradiation. The FA-free sample undergoes more color degradation compared to samples containing FA. The coating with 2% FA has the most stable color with chromaticity of 41% and color saturation of 0.88 compared to other FA containing coats. The FA-free coat exhibits 29% chromaticity and color saturation of 0.38 at the end of the experiment.

  9. Red chicory (Cichorium intybus L. cultivar) as a potential source of antioxidant anthocyanins for intestinal health.

    D'evoli, Laura; Morroni, Fabiana; Lombardi-Boccia, Ginevra; Lucarini, Massimo; Hrelia, Patrizia; Cantelli-Forti, Giorgio; Tarozzi, Andrea

    2013-01-01

    Fruit- and vegetable-derived foods have become a very significant source of nutraceutical phytochemicals. Among vegetables, red chicory (Cichorium Intybus L. cultivar) has gained attention for its content of phenolic compounds, such as the anthocyanins. In this study, we evaluated the nutraceutical effects, in terms of antioxidant, cytoprotective, and antiproliferative activities, of extracts of the whole leaf or only the red part of the leaf of Treviso red chicory (a typical Italian red leafy plant) in various intestinal models, such as Caco-2 cells, differentiated in normal intestinal epithelia and undifferentiated Caco-2 cells. The results show that the whole leaf of red chicory can represent a good source of phytochemicals in terms of total phenolics and anthocyanins as well as the ability of these phytochemicals to exert antioxidant and cytoprotective effects in differentiated Caco-2 cells and antiproliferative effects in undifferentiated Caco-2 cells. Interestingly, compared to red chicory whole leaf extracts, the red part of leaf extracts had a significantly higher content of both total phenolics and anthocyanins. The same extracts effectively corresponded to an increase of antioxidant, cytoprotective, and antiproliferative activities. Taken together, these findings suggest that the red part of the leaf of Treviso red chicory with a high content of antioxidant anthocyanins could be interesting for development of new food supplements to improve intestinal health. PMID:24069504

  10. Microencapsulation of saffron petal anthocyanins with cress seed gum compared with Arabic gum through freeze drying.

    Jafari, Seid-Mahdi; Mahdavi-Khazaei, Katayoun; Hemmati-Kakhki, Abbas

    2016-04-20

    In this research, encapsulation efficiency of cress seed gum (CSG) as a native hydrocolloid was compared with Arabic gum (AG) and maltodextrin (dextrose equivalent of 20 (M20), and 7 (M7)) for saffron (Crocus sativus) petal's extract by freeze drying method. Combinations of CSG-M20, AG-M20, and M7-M20 with ratios of 50:50 and M20 alone (100%) were used as wall materials. A mixture of 1:5 (based on dry matter) between core (concentrated anthocyanin extract of saffron petal) and wall materials were freeze dried and stability of encapsulated anthocyanins along with color parameters (a*, b*, L*, C, H° and TCD) of final powders were measured during 10 weeks of storage (at 35°C as an accelerated method). Total anthocyanins were determined through pH differential method every week. Four prepared formulations of encapsulated powders didn't show any significant differences (P>0.01) in terms of total anthocyanin content measured immediately after production and after 10 weeks storage. AG-M20 mixture and M20 alone showed the highest and lowest TCD, respectively. The mixture of CSG-M20 in comparison with AG-M20 and M20 had the same protecting effect (P<0.01) but showed a relatively high TCD (9.33). PMID:26876823

  11. Cucurbit[7]uril inclusion complexation as a supramolecular strategy for color stabilization of anthocyanin model compounds.

    Held, Barbara; Tang, Hao; Natarajan, Palani; da Silva, Cassio Pacheco; de Oliveira Silva, Volnir; Bohne, Cornelia; Quina, Frank H

    2016-06-01

    Host-guest complexation with cucurbit[7]uril of anthocyanin model compounds in which acid-base equilibria are blocked resulted in essentially complete stabilization of their color. The color protection is a thermodynamic effect and establishes a strategy to stabilize these colored compounds at pH values of interest for practical applications. PMID:27123548

  12. Spectral-optical characteristics of anthocyanin-containing natural dye staff

    Spectral-optical characteristics of anthocyanin-containing natural dye staff received from fruit ficus carica are determined. The chromatographic separating of dyeing pigment obtained is performed. The data obtained can be used as passport characteristics of the new food dye staff. (authors)

  13. Development of a Recombinant Escherichia coli Strain for Overproduction of the Plant Pigment Anthocyanin.

    Lim, Chin Giaw; Wong, Lynn; Bhan, Namita; Dvora, Hila; Xu, Peng; Venkiteswaran, Sankaranarayanan; Koffas, Mattheos A G

    2015-09-01

    Anthocyanins are water-soluble colored pigments found in terrestrial plants and are responsible for the red, blue, and purple coloration of many flowers and fruits. In addition to the plethora of health benefits associated with anthocyanins (cardioprotective, anti-inflammatory, antioxidant, and antiaging properties), these compounds have attracted widespread attention due to their promising potential as natural food colorants. Previously, we reported the biotransformation of anthocyanin, specifically cyanidin 3-O-glucoside (C3G), from the substrate (+)-catechin in Escherichia coli. In the present work, we set out to systematically improve C3G titers by enhancing substrate and precursor availability, balancing gene expression level, and optimizing cultivation and induction parameters. We first identified E. coli transporter proteins that are responsible for the uptake of catechin and secretion of C3G. We then improved the expression of the heterologous pathway enzymes anthocyanidin synthase (ANS) and 3-O-glycosyltransferase (3GT) using a bicistronic expression cassette. Next, we augmented the intracellular availability of the critical precursor UDP-glucose, which has been known as the rate-limiting precursor to produce glucoside compounds. Further optimization of culture and induction conditions led to a final titer of 350 mg/liter of C3G. We also developed a convenient colorimetric assay for easy screening of C3G overproducers. The work reported here constitutes a promising foundation to develop a cost-effective process for large-scale production of plant-derived anthocyanin from recombinant microorganisms. PMID:26150456

  14. Solid-phase extraction of berries’ anthocyanins and evaluation of their antioxidative properties

    Denev, P.; Číž, Milan; Ambrožová, Gabriela; Lojek, Antonín; Yanakieva, I.; Kratchanova, M.

    2010-01-01

    Roč. 123, č. 4 (2010), s. 1055-1061. ISSN 0308-8146 R&D Projects: GA MŠk(CZ) OC08058 Institutional research plan: CEZ:AV0Z50040507; CEZ:AV0Z50040702 Keywords : anthocyanins * solid-phase extraction * berry extracts Subject RIV: BO - Biophysics Impact factor: 3.458, year: 2010

  15. Assessment of anthocyanin and agronomic trait variation in some commonly used medicinal legumes

    Several legumes including Canavalia ensiformis, Desmodium adscendens, Indigofera suffruticosa, Senna covesii, and S. occidentalis are currently used as medicinal plants. These species contain anthocyanins as well with potential to be used in the pharmaceutical markets. The USDA, ARS, Plant Genetic R...

  16. Effect of solvent and temperature on pressurized fluid extraction of anthocyanins from red grape skin

    Hohnová, Barbora; Šťavíková, L.; Karásek, Pavel

    2008. s. 443-443. ISBN -. [International Symposium on Capillary Chromatography /32./ and GCxGC Symposium /5./. 26.05.2008-30.05.2008, Riva del Garda] R&D Projects: GA ČR GA203/08/1536 Institutional research plan: CEZ:AV0Z40310501 Keywords : PFE * anthocyanins * red grape Subject RIV: CB - Analytical Chemistry, Separation

  17. Anthocyanins do not influence long-chain n-3 fatty acid status: studies in cells, rodents and humans.

    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

    2015-03-01

    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

  18. TiO2 dye sensitized solar cell (DSSC): linear relationship of maximum power point and anthocyanin concentration

    Ahmadian, Radin

    2010-09-01

    This study investigated the relationship of anthocyanin concentration from different organic fruit species and output voltage and current in a TiO2 dye-sensitized solar cell (DSSC) and hypothesized that fruits with greater anthocyanin concentration produce higher maximum power point (MPP) which would lead to higher current and voltage. Anthocyanin dye solution was made with crushing of a group of fresh fruits with different anthocyanin content in 2 mL of de-ionized water and filtration. Using these test fruit dyes, multiple DSSCs were assembled such that light enters through the TiO2 side of the cell. The full current-voltage (I-V) co-variations were measured using a 500 Ω potentiometer as a variable load. Point-by point current and voltage data pairs were measured at various incremental resistance values. The maximum power point (MPP) generated by the solar cell was defined as a dependent variable and the anthocyanin concentration in the fruit used in the DSSC as the independent variable. A regression model was used to investigate the linear relationship between study variables. Regression analysis showed a significant linear relationship between MPP and anthocyanin concentration with a p-value of 0.007. Fruits like blueberry and black raspberry with the highest anthocyanin content generated higher MPP. In a DSSC, a linear model may predict MPP based on the anthocyanin concentration. This model is the first step to find organic anthocyanin sources in the nature with the highest dye concentration to generate energy.

  19. In the Solanaceae, a hierarchy of bHLHs confer distinct target specificity to the anthocyanin regulatory complex

    Montefiori, Mirco; Brendolise, Cyril; Dare, Andrew P; Lin-Wang, Kui; Davies, Kevin M.; Hellens, Roger P; Andrew C. Allan

    2015-01-01

    The anthocyanin biosynthetic pathway is regulated by a transcription factor complex consisting of an R2R3 MYB, a bHLH, and a WD40. Although R2R3 MYBs belonging to the anthocyanin-activating class have been identified in many plants, and their role well elucidated, the subgroups of bHLH implicated in anthocyanin regulation seem to be more complex. It is not clear whether these potential bHLH partners are biologically interchangeable with redundant functions, or even if heterodimers are involve...

  20. Control of Anthocyanin Synthesis in PETUNIA HYBRIDA by Multiple Allelic Series of the Genes An1 and An2

    Gerats, Anton G. M.; Farcy, Eliane; Wallroth, Marco; Groot, Steven P. C.; Schram, André

    1984-01-01

    A mutable allele of the An1 locus in Petunia hybrida has given rise to a multiple series of stable derivative alleles. Anthocyanin concentration in mature flowers of these mutants (an1+/ p/an1) decreases from the wild-type red to the recessive white in a continuous series. Anthocyanin composition changes regularly: the ratio of peonidin to cyanidin is 3.5 for an an1+/+/ an1 and 1.2 for an an1+/p5/an1 mutant. Analysis of anthocyanins during flower development indicates that these differences ...

  1. Research progress in anthocyanin in raspberry%树莓花色苷研究进展

    王远辉; 王洪新

    2011-01-01

    Raspberry fruit was rich in anthocyanin, the structure of raspberry anthocyanins had their special characteristics. Raspberry anthocyanins had a variety of biological activity and were paid attention by food,pharmaceutics,cosmetics and other industries. At persent, domestic and foreign experts and scholars had done some interesting researches to lay solid theoretical foundation for the development and utilization of raspberry anthocyanins,but there were still many key areas to be explore. This paper introduced research status of raspberry anthocyanins about extraction, purification, biological activity, metabolism, and stability in recent years, and provided a reference for in-depth study in the future.%树莓果实富含花色苷,树莓花色苷具有自身结构特点,已被证实有多种生理活性,受到食品、药品、化妆品等行业青睐.迄今为止国内外专家学者对树莓花色苷做了一些有意义的研究,为树莓花色苷的开发利用奠定了坚实理论基础,但仍有许多关键领域要探索.本文介绍了近十年关于树莓花色苷提取、分离纯化、生理活性、代谢和稳定性等方面的研究现状,为以后深入研究提供参考.

  2. ACIDIC SOAKING AND STEAM BLANCHING RETAIN ANTHOCYANINS AND POLYPHENOLS IN PURPLE Dioscorea alata FLOUR

    Nelis Imanningsih*

    2013-12-01

    Full Text Available Purple Dioscorea alata (DA tuber has health benefits due to its bioactive anthocyanins, which belong to polyphenolic group. Tuber is commonly made into flour to optimize its uses, however, the anthocyanins undergo significant degradation during processing because of the endogenous polyphenol oxidase activities. This research investigated factors that retain anthocyanins and polyphenols in the purple DA flour as well as its antioxidant capacity. The types of treatments during milling process should be taken into account; for instance, soaking in citric acid and blanching in order to preserve the bioactive compounds. To examine the inhibitory effects of acidic soaking and steam blanching on polyphenol oxidase activities, these experiments used four levels of citric acid (0, 0.25, 0.5, and 1% and two levels of steam blanching time course (5 and 10 minutes. It was found that steam blanching for 5 or 10 minutes could reduce the activity of polyphenol oxidase, and consequently, retard the oxidation process and retain the polyphenolic compounds. Soaking the purple DA slices into a 1% citric acid solution followed by steam blanching for 10 min resulted in the highest total anthocyanins (104.36 mg/100 g, polyphenols (198.52 mg equivalent gallic acid/100 g, with an antioxidant capacity of 1.300 mg trolox equivalent/100 g. This study showed that the retention of bioactive compounds of DA tuber through soaking the tuber slices in solution containing inexpensive chemicals like citric acid at low concentrations, combined with 10 minutes of steam blanching resulted in flour containing total anthocyanins and phenolic as high as 44.51 and 62.58% of fresh tuber, respectively.

  3. Toxicity of Carboxylic Acid-Containing Drugs: The Role of Acyl Migration and CoA Conjugation Investigated.

    Lassila, Toni; Hokkanen, Juho; Aatsinki, Sanna-Mari; Mattila, Sampo; Turpeinen, Miia; Tolonen, Ari

    2015-12-21

    Many carboxylic acid-containing drugs are associated with idiosyncratic drug toxicity (IDT), which may be caused by reactive acyl glucuronide metabolites. The rate of acyl migration has been earlier suggested as a predictor of acyl glucuronide reactivity. Additionally, acyl Coenzyme A (CoA) conjugates are known to be reactive. Here, 13 drugs with a carboxylic acid moiety were incubated with human liver microsomes to produce acyl glucuronide conjugates for the determination of acyl glucuronide half-lives by acyl migration and with HepaRG cells to monitor the formation of acyl CoA conjugates, their further conjugate metabolites, and trans-acylation products with glutathione. Additionally, in vitro cytotoxicity and mitochondrial toxicity experiments were performed with HepaRG cells to compare the predictability of toxicity. Clearly, longer acyl glucuronide half-lives were observed for safe drugs compared to drugs that can cause IDT. Correlation between half-lives and toxicity classification increased when "relative half-lives," taking into account the formation of isomeric AG-forms due to acyl migration and eliminating the effect of hydrolysis, were used instead of plain disappearance of the initial 1-O-β-AG-form. Correlation was improved further when a daily dose of the drug was taken into account. CoA and related conjugates were detected primarily for the drugs that have the capability to cause IDT, although some exceptions to this were observed. Cytotoxicity and mitochondrial toxicity did not correlate to drug safety. On the basis of the results, the short relative half-life of the acyl glucuronide (high acyl migration rate), high daily dose and detection of acyl CoA conjugates, or further metabolites derived from acyl CoA together seem to indicate that carboxylic acid-containing drugs have a higher probability to cause drug-induced liver injury (DILI). PMID:26558897

  4. Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber

    Na Gao

    2012-08-01

    Full Text Available Fucosylated chondroitin sulfate (FuCS, a kind of complex glycosaminoglycan from sea cucumber, has potent anticoagulant activity. In order to understand the relationship between structures and activity, the depolymerized FuCS (dFuCS was chosen to prepare its derivates by selective substitution at OH groups. Its O-acylation was carried out in a homogeneous way using carboxylic acid anhydrides. The structures of O-acylated derivatives were characterized by NMR. The results indicated that the 4-O-sulfated fucose residues may be easier to be acylated than the other ones in the sulfated fucose branches. But the O-acylation was always accompanied by the β-elimination, and the degree of elimination was higher as that of acylation was higher. The results of clotting assay indicated that the effect of partial O-acylation of the dFuCS on their anticoagulant potency was not significant and the O-acylation of 2-OH groups of 4-O-sulfated fucose units did not affect the anticoagulant activity.

  5. Acyl-Homoserine Lactone Quorum Sensing in the Roseobacter Clade

    Jindong Zan

    2014-01-01

    Full Text Available Members of the Roseobacter clade are ecologically important and numerically abundant in coastal environments and can associate with marine invertebrates and nutrient-rich marine snow or organic particles, on which quorum sensing (QS may play an important role. In this review, we summarize current research progress on roseobacterial acyl-homoserine lactone-based QS, particularly focusing on three relatively well-studied representatives, Phaeobacter inhibens DSM17395, the marine sponge symbiont Ruegeria sp. KLH11 and the dinoflagellate symbiont Dinoroseobacter shibae. Bioinformatic survey of luxI homologues revealed that over 80% of available roseobacterial genomes encode at least one luxI homologue, reflecting the significance of QS controlled regulatory pathways in adapting to the relevant marine environments. We also discuss several areas that warrant further investigation, including studies on the ecological role of these diverse QS pathways in natural environments.

  6. Small Antimicrobial Agents Based on Acylated Reduced Amide Scaffold.

    Teng, Peng; Huo, Da; Nimmagadda, Alekhya; Wu, Jianfeng; She, Fengyu; Su, Ma; Lin, Xiaoyang; Yan, Jiyu; Cao, Annie; Xi, Chuanwu; Hu, Yong; Cai, Jianfeng

    2016-09-01

    Prevalence of drug-resistant bacteria has emerged to be one of the greatest threats in the 21st century. Herein, we report the development of a series of small molecular antibacterial agents that are based on the acylated reduced amide scaffold. These molecules display good potency against a panel of multidrug-resistant Gram-positive and Gram-negative bacterial strains. Meanwhile, they also effectively inhibit the biofilm formation. Mechanistic studies suggest that these compounds kill bacteria by compromising bacterial membranes, a mechanism analogous to that of host-defense peptides (HDPs). The mechanism is further supported by the fact that the lead compounds do not induce resistance in MRSA bacteria even after 14 passages. Lastly, we also demonstrate that these molecules have therapeutic potential by preventing inflammation caused by MRSA induced pneumonia in a rat model. This class of compounds could lead to an appealing class of antibiotic agents combating drug-resistant bacterial strains. PMID:27526720

  7. Mellemkaedet acyl-CoA dehydrogenase (MCAD)-mangel

    Gregersen, N; Winter, V; Andresen, B S;

    1992-01-01

    today considered more common than previously anticipated, since the incidence of patients with MCAD enzyme deficiency in Denmark is estimated to 1/27,000 newborns, or two new cases annually. The relationship between the enzyme defect (gene defect) and the clinical expression of the disease is a main......Medium-chain acyl-CoA dehydrogenase (MCAD) deficiency is a potentially fatal metabolic disease, which is characterized by non-ketotic hypoglycemia and lethargy. The disease manifests itself by periodic attacks in connection with infections and periods of fasting, or suddenly as unexpected child......-card constitute today a certain and specific diagnosis for the disease in 75% of all cases. In the remaining 25% the mutation analysis is supplemented with urine metabolite studies by gas chromatography/mass spectrometry, and with measurements of enzyme activities in cultured skin fibroblasts. The disease is...

  8. Synthesis of acyl derivatives of salicin, salirepin, and arbutin.

    Stepanova, Elena V; Belyanin, Maxim L; Filimonov, Victor D

    2014-03-31

    The total synthesis of two natural phenolglycosides of the family Salicaceae, namely: populoside and 2-(β-d-glucopyranosyloxy)-5-hydroxy benzyl (3-methoxy-4-hydroxy) cinnamoate and nine not found yet in plants acyl derivatives of phenoglycosides: 2-(β-d-glucopyranosyloxy)-benzylcinnamoate, 2-(β-d-glucopyranosyloxy)-benzyl (4-hydroxy) benzoate, 2-(β-d-glucopyranosyloxy)-benzyl (3-methoxy-4-hydroxy) benzoate, 2-(β-d-glucopyranosyloxy)-5-hydroxy benzyl (3,4-dihydroxy) cinnamoate, 2-(β-d-glucopyranosyloxy)-5-hydroxy benzylcinnamoate, 2-(β-d-glucopyranosyloxy)-5-hydroxy benzyl (4-hydroxy) benzoate, 2-(β-d-glucopyranosyloxy)-5-hydroxy benzyl (3-methoxy-4-hydroxy) benzoate, 2-(β-d-glucopyranosyloxy)-5-benzoyloxy benzylbenzoate and 4-(β-d-glucopyranosyloxy)-phenylbenzoate, starting from readily available phenols and glucose was developed for the first time. PMID:24632218

  9. An acylated phloroglucinol with antimicrobial properties from Helichrysum caespititium.

    Mathekga, A D; Meyer, J J; Horn, M M; Drewes, S E

    2000-01-01

    A new acylated form of a phloroglucinol with significant antimicrobial properties was isolated by bioactivity guided fractionation from Helichrysum caespititium (Asteraceae). The structure elucidation, and conformation of the new phloroglucinol, 2-methyl-4-[2',4',6'-trihydroxy-3'-(2-methylpropanoyl) phenyl]but-2-enyl acetate, was established by high field NMR spectroscopic and MS data. The compound inhibited growth of Bacillus cereus, B. pumilus, B. subtilis and Micrococcus kristinae at the very low concentration of 0.5 microg/ml and Staphylococcus aureus at 5.0 microg/ml. Six fungi tested were similarly inhibited at low MICs, Aspergillus flavus and A. niger (1.0 microg/ml), Cladosporium chladosporioides (5 microg/ml), C. cucumerinum and C. sphaerospermum (0.5 microg/ml) and Phylophthora capsici at 1.0 microg/ml. PMID:10656414

  10. Changes in antioxidant enzymes activities and proline, total phenol and anthocyanine contents in Hyssopus officinalis L. plants under salt stress.

    Jahantigh, Omolbanin; Najafi, Farzaneh; Badi, Hassanali Naghdi; Khavari-Nejad, Ramazan Ali; Sanjarian, Forough

    2016-06-01

    The relationships between salt stress and antioxidant enzymes activities, proline, phenol and anthocyanine contents in Hyssopus officinalis L. plants in growth stage were investigated. The plants were subjected to five levels of saline irrigation water, 0.37 (tap water as control) with 2, 4, 6, 8 and 10 dSm(-1) of saline water. After two months the uniform plants were harvested for experimental analysis. Antioxidant enzymes activities and proline, phenol and anthocyanine contents of the plants were examinated. Enhanced activities of peroxidase, catalase and superoxide dismutase were determined by increasing salinity that plays an important protective role in the ROS-scavenging process. Proline, phenol and anthocyanine contents increased significantly with increasing salinity. These results suggest that salinity tolerance of Hyssopus officinalis plants might be closely related with the increased capacity of antioxidative system to scavenge reactive oxygen species and with the accumulation of osmoprotectant proline, phenol and anthocyanine contents under salinity conditions. PMID:27165530

  11. Correction: Cucurbit[7]uril inclusion complexation as a supramolecular strategy for color stabilization of anthocyanin model compounds.

    Held, Barbara; Tang, Hao; Natarajan, Palani; Silva, Cassio Pacheco da; Silva, Volnir de Oliveira; Bohne, Cornelia; Quina, Frank H

    2016-06-01

    Correction for 'Cucurbit[7]uril inclusion complexation as a supramolecular strategy for color stabilization of anthocyanin model compounds' by Barbara Held, et al., Photochem. Photobiol. Sci., 2016, DOI: 10.1039/c6pp00060f. PMID:27216443

  12. Exogenous application of pectin-derived oligosaccharides to grape berries modifies anthocyanin accumulation, composition and gene expression.

    Villegas, Daniel; Handford, Michael; Alcalde, José Antonio; Perez-Donoso, Alonso

    2016-07-01

    Anthocyanins are secondary metabolites synthesized in grape berry skins via the phenylpropanoid pathway, with functions ranging from skin coloration to protection against pathogens or UV light. Accumulation of these compounds is highly variable depending on genetics, environmental factors and viticultural practices. Besides their biological functions, anthocyanins improve wine quality, as a high anthocyanin content in berries has a positive impact on the color, total phenolic concentration and, ultimately, the price of wine. The present work studies the effect of the pre-veraison application of pectin derived oligosaccharides (PDO) on the synthesis and accumulation of these compounds, and associates the changes observed with the expression of key genes in the phenylpropanoid pathways. To this end, pre-veraison Cabernet Sauvignon bunches were treated with PDO to subsequently determine total anthocyanin content, the anthocyanin profile (by HPLC-DAD) and gene expression (by qRT-PCR), using Ethrel and water treatments for comparison. The results show that PDO were as efficient as Ethrel in generating a significant rise in total anthocyanin content at 30 days after treatment (dat), compared with water treatments (1.32, 1.48 and 1.02 mg e.Mv-3G/g FW respectively) without any undesirable effect on berry size, soluble solids, tartaric acid concentration or pH. In addition, a significant alteration in the anthocyanin profile was observed. Specifically, a significant increase in the relative concentration of malvidin was observed for both PDO and Ethrel treatments, compared with water controls (52.8; 55.0 and 48.3%, respectively), with a significant rise in tri-hydroxylated forms and a fall in di-hydroxylated anthocyanins. The results of gene expression analyses suggest that the increment in total anthocyanin content is related to a short term increase in phenylalanine ammonia-lyase (PAL) expression, mediated by a decrease in MYB4A expression. A longer term increase in UDP

  13. Interfacial Behavior of Fatty-Acylated Sericin Prepared by Lipase-Catalyzed Solid-Phase Synthesis

    Ogino, Masato; Tanaka, Rie; 服部, 誠; Yoshida, Tadashi; 横手, よし子; 高橋, 幸資

    2006-01-01

    Fatty-acylated sericin {1:0.7 molar ratio of sericin (Mr 18,700) to oleic acid} was prepared by lipase-catalyzed solid-phase synthesis in n-hexane containing oleic acid to endow sericin with interfacial properties. Acylation with oleic acid was confirmed by 1H-NMR. The fatty-acylated sericin exhibited superior emulsifying activity index and emulsion stability in the presence of 0?0.5 M NaCl, in a temperature range of 30?80 °C and pH range of 2?7, as compared with the control sericin. The fatt...

  14. Melatonin Improved Anthocyanin Accumulation by Regulating Gene Expressions and Resulted in High Reactive Oxygen Species Scavenging Capacity in Cabbage

    Zhang, Na; Sun, Qianqian; Li, Hongfei; Li, Xingsheng; Cao, Yunyun; Zhang, Haijun; Li, Shuangtao; Zhang, Lei; Qi, Yan; Ren, Shuxin; Zhao, Bing; Guo, Yang-Dong

    2016-01-01

    In this work, we found, that exogenous melatonin pretreatment improved anthocyanin accumulation (1- to 2-fold) in cabbage. To verify the relationship with melatonin and anthocyanin, an Arabidopsis mutant, snat, which expresses a defective form of the melatonin biosynthesis enzyme SNAT (Serotonin N-acetyl transferase), was employed. Under cold conditions, the foliage of wild-type Arabidopsis exhibited a deeper red color than the snat mutant. This finding further proved, that exogenous melatoni...

  15. Computational Identification of Anthocyanin-Specific Transcription Factors using a Rice Microarray and Maximum Boundary Range Algorithm

    Chang Kug Kim; Shoshi Kikuchi; Jang Ho Hahn; Soo Chul Park; Yong Hwan Kim; Byun Woo Lee

    2010-01-01

    This study identifies 2,617 candidate genes related to anthocyanin biosynthesis in rice using microarray analysis and a newly developed maximum boundary range algorithm. Three seed developmental stages were examined in white cultivar and two black Dissociation insertion mutants. The resultant 235 transcription factor genes found to be associated with anthocyanin were classified into nine groups. It is compared the 235 genes by transcription factor analysis and 593 genes from among clusters of...

  16. The Arabidopsis thaliana mutant air1 implicates SOS3 in the regulation of anthocyanins under salt stress

    Van Oosten, Michael James

    2013-08-08

    The accumulation of anthocyanins in plants exposed to salt stress has been largely documented. However, the functional link and regulatory components underlying the biosynthesis of these molecules during exposure to stress are largely unknown. In a screen of second site suppressors of the salt overly sensitive3-1 (sos3-1) mutant, we isolated the anthocyanin-impaired-response-1 (air1) mutant. air1 is unable to accumulate anthocyanins under salt stress, a key phenotype of sos3-1 under high NaCl levels (120 mM). The air1 mutant showed a defect in anthocyanin production in response to salt stress but not to other stresses such as high light, low phosphorous, high temperature or drought stress. This specificity indicated that air1 mutation did not affect anthocyanin biosynthesis but rather its regulation in response to salt stress. Analysis of this mutant revealed a T-DNA insertion at the first exon of an Arabidopsis thaliana gene encoding for a basic region-leucine zipper transcription factor. air1 mutants displayed higher survival rates compared to wild-type in oxidative stress conditions, and presented an altered expression of anthocyanin biosynthetic genes such as F3H, F3′H and LDOX in salt stress conditions. The results presented here indicate that AIR1 is involved in the regulation of various steps of the flavonoid and anthocyanin accumulation pathways and is itself regulated by the salt-stress response signalling machinery. The discovery and characterization of AIR1 opens avenues to dissect the connections between abiotic stress and accumulation of antioxidants in the form of flavonoids and anthocyanins. © 2013 Springer Science+Business Media Dordrecht.

  17. Characterization of the regulatory network of BoMYB2 in controlling anthocyanin biosynthesis in purple cauliflower.

    Chiu, Li-Wei; Li, Li

    2012-10-01

    Purple cauliflower (Brassica oleracea L. var. botrytis) Graffiti represents a unique mutant in conferring ectopic anthocyanin biosynthesis, which is caused by the tissue-specific activation of BoMYB2, an ortholog of Arabidopsis PAP2 or MYB113. To gain a better understanding of the regulatory network of anthocyanin biosynthesis, we investigated the interaction among cauliflower MYB-bHLH-WD40 network proteins and examined the interplay of BoMYB2 with various bHLH transcription factors in planta. Yeast two-hybrid studies revealed that cauliflower BoMYBs along with the other regulators formed the MYB-bHLH-WD40 complexes and BobHLH1 acted as a bridge between BoMYB and BoWD40-1 proteins. Different BoMYBs exhibited different binding activity to BobHLH1. Examination of the BoMYB2 transgenic lines in Arabidopsis bHLH mutant backgrounds demonstrated that TT8, EGL3, and GL3 were all involved in the BoMYB2-mediated anthocyanin biosynthesis. Expression of BoMYB2 in Arabidopsis caused up-regulation of AtTT8 and AtEGL3 as well as a subset of anthocyanin structural genes encoding flavonoid 3'-hydroxylase, dihydroflavonol 4-reductase, and leucoanthocyanidin dioxygenase. Taken together, our results show that MYB-bHLH-WD40 network transcription factors regulated the bHLH gene expression, which may represent a critical feature in the control of anthocyanin biosynthesis. BoMYB2 together with various BobHLHs specifically regulated the late anthocyanin biosynthetic pathway genes for anthocyanin biosynthesis. Our findings provide additional information for the complicated regulatory network of anthocyanin biosynthesis and the transcriptional regulation of transcription factors in vegetable crops. PMID:22644767

  18. A bHLH transcription factor, DvIVS, is involved in regulation of anthocyanin synthesis in dahlia (Dahlia variabilis)

    Ohno, Sho; Hosokawa, Munetaka; Hoshino, Atsushi; Kitamura, Yoshikuni; Morita, Yasumasa; Park, Kyeung-II; Nakashima, Akiko; Deguchi, Ayumi; Tatsuzawa, Fumi; Doi, Motoaki; Iida, Shigeru; Yazawa, Susumu

    2011-01-01

    Dahlias (Dahlia variabilis) exhibit a wide range of flower colours because of accumulation of anthocyanin and other flavonoids in their ray florets. Two lateral mutants were used that spontaneously occurred in ‘Michael J’ (MJW) which has yellow ray florets with orange variegation. MJOr, a bud mutant producing completely orange ray florets, accumulates anthocyanins, flavones, and butein, and MJY, another mutant producing completely yellow ray florets, accumulates flavones and butein. Reverse t...

  19. A bHLH transcription factor, DvIVS, is involved in regulation of anthocyanin synthesis in dahlia (Dahlia variabilis).

    Ohno, Sho; Hosokawa, Munetaka; Hoshino, Atsushi; Kitamura, Yoshikuni; Morita, Yasumasa; Park, Kyeung-II; Nakashima, Akiko; Deguchi, Ayumi; Tatsuzawa, Fumi; Doi, Motoaki; Iida, Shigeru; Yazawa, Susumu

    2011-01-01

    Dahlias (Dahlia variabilis) exhibit a wide range of flower colours because of accumulation of anthocyanin and other flavonoids in their ray florets. Two lateral mutants were used that spontaneously occurred in 'Michael J' (MJW) which has yellow ray florets with orange variegation. MJOr, a bud mutant producing completely orange ray florets, accumulates anthocyanins, flavones, and butein, and MJY, another mutant producing completely yellow ray florets, accumulates flavones and butein. Reverse t...

  20. Use of image analysis to estimate anthocyanin and UV-excited fluorescent phenolic compound levels in strawberry fruit

    YOSHIOKA, YOSUKE; Nakayama, Masayoshi; Noguchi, Yuji; Horie, Hideki

    2013-01-01

    Strawberry is rich in anthocyanins, which are responsible for the red color, and contains several colorless phenolic compounds. Among the colorless phenolic compounds, some, such as hydroxycinammic acid derivatives, emit blue-green fluorescence when excited with ultraviolet (UV) light. Here, we investigated the effectiveness of image analyses for estimating the levels of anthocyanins and UV-excited fluorescent phenolic compounds in fruit. The fruit skin and cut surface of 12 cultivars were ph...

  1. Neuroprotective effects of anthocyanin- and proanthocyanidin-rich extracts in cellular models of Parkinson’s disease

    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

    2014-01-01

    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 rotenon...

  2. Comparative analyses of light-induced anthocyanin accumulation and gene expression between the ray florets and leaves in chrysanthemum.

    Hong, Yan; Yang, Li-Wen; Li, Meng-Ling; Dai, Si-Lan

    2016-06-01

    Light is one of the key environmental factors that affect anthocyanin biosynthesis. However, the underlying molecular mechanism remains unclear, and many problems regarding phenotypic change and corresponding gene regulation have not been solved. In the present study, comparative analyses of light-induced anthocyanin accumulation and gene expression between the ray florets and leaves were performed in Chrysanthemum × morifolium 'Purple Reagan'. After contrasting the variations in the flower color phenotype and relative pigment content, as well as expression patterns of structural and regulator genes responsible for anthocyanin biosynthesis and photoreceptor between different plant organs under light and dark conditions, we concluded that (1) both the capitulum and foliage are key organs responding to light for chrysanthemum coloration; (2) compared with flavones, shading makes a greater decrease on the anthocyanins accumulation; (3) most of the structural and regulatory genes in the light-induced anthocyanin pathway specifically express in the ray florets; and (4) CmCHS, CmF3H, CmF3'H, CmANS, CmDFR, Cm3GT, CmMYB5-1, CmMYB6, CmMYB7-1, CmbHLH24, CmCOP1 and CmHY5 are key genes for light-induced anthocyanin biosynthesis in chrysanthemum ray florets, while on the transcriptional level, the expressions of CmPHYA, CmPHYB, CmCRY1a, CmCRY1b and CmCRY2 are insignificantly changed. Moreover, the inferred comprehensive effect of multiple signals on the accumulation of anthocyanins and transmission channel of light signal that exist between the leaves and ray florets were further discussed. These results further our understanding of the relationship between the gene expression and light-induced anthocyanin biosynthesis, and lay foundations for the promotion of the molecular breeding of novel flower colors in chrysanthemums. PMID:26990403

  3. Thermal and pH degradation kinetics of anthocyanins in natural food colorant prepared from black rice bran.

    Loypimai, Patiwit; Moongngarm, Anuchita; Chottanom, Pheeraya

    2016-01-01

    The study of the stability of anthocyanins in food colorant powder is important to predict the quality changes occurring as the food products are processed, to prevent and control the degradation of the anthocyanins. The objectives of this study were to identify anthocyanin components in natural food colorants obtained from black rice bran, and investigate their thermal stability at 60, 80, and 100 °C, pH stability from 2.0 to 5.0 and also their correlation with visual color, L (*), C (*), and h°. Results showed that only six types of anthocyanins, cyanidin-3-O-glucoside, cyanidin-3-O-rutinoside, delphinidin, cyanidin, pelargonidin and malvidin were present in raw black rice bran (BRB) and black rice bran colorant powder (BCP). The thermal degradation of both the visual color and the anthocyanin content in the BCP followed a first-order kinetic reaction model. The temperature-dependent degradation was adequately fitted to the Arrhenius equation. In terms of the pH stability, increasing pH values resulted in lower activation energies (E a ) and higher half-life (t 1/2 ) values for both color parameters and individual anthocyanins when heating from 60 to 100 °C. Moreover, the degradation rate constant (k) increased with increasing temperature and pH value. The degradation of cyanidin-3-O-glucoside and total anthocyanins showed a strong positive correlation with C (*). The changes in visual color may be used as an on-line quality control indicator during thermal processing of food products containing rice bran colorants which have high anthocyanin content. PMID:26787965

  4. Use of Modified Phenolic Thyme Extracts (Thymus vulgaris) with Reduced Polyphenol Oxidase Substrates as Anthocyanin Color and Stability Enhancing Agents

    Oscar Aguilar; Carmen Hernández-Brenes

    2015-01-01

    Residual enzymatic activity in certain foods, particularly of polyphenoloxidase (PPO), is responsible for the majority of anthocyanin degradation in food systems, causing also parallel losses of other relevant nutrients. The present work explored the feasibility of modifying phenolic profiles of thyme extracts, by use of chromatographic resins, to obtain phenolic extracts capable of enhancing anthocyanin colour and stability in the presence of PPO activity. Results indicated that pretreatment...

  5. Anthocyanin and Carotenoid Contents in Different Cultivars of Chrysanthemum (Dendranthema grandiflorum Ramat. Flower

    Chang Ha Park

    2015-06-01

    Full Text Available The flowers of twenty-three cultivars of Dendranthema grandiflorum Ramat. were investigated to determine anthocyanin and carotenoid levels and to confirm the effects of the pigments on the flower colors using high-performance liquid chromatography (HPLC and electrospray ionization-mass spectrometry (ESI-MS. The cultivars contained the anthocyanins cyanidin 3-glucoside (C3g and cyanidin 3-(3ʺ-malonoyl glucoside (C3mg and the following carotenoids: lutein, zeaxanthin, β-cryptoxanthin, 13-cis-β-carotene, α-carotene, trans-β-carotene, and 9-cis-β-carotene. The cultivar “Magic” showed the greatest accumulation of total and individual anthocyanins, including C3g and C3gm. On the other hand, the highest level of lutein and zeaxanthin was noted in the cultivar “Il Weol”. The cultivar “Anastasia” contained the highest amount of carotenoids such as trans-β-carotene, 9-cis-β-carotene, and 13-cis-β-carotene. The highest accumulation of β-cryptoxanthin and α-carotene was noted in the cultivar “Anastasia” and “Il Weol”. Our results suggested that ‘Magic”, “Angel” and “Relance’ had high amounts of anthocyanins and showed a wide range of red and purple colors in their petals, whereas “Il Weol’, “Popcorn Ball’ and “Anastasia” produced higher carotenoid contents and displayed yellow or green petal colors. Interestingly, “Green Pang Pang”, which contained a high level of anthocyanins and a medium level of carotenoids, showed the deep green colored petals. “Kastelli”, had high level of carotenoids as well as a medium level of anthocyanins and showed orange and red colored petals. It was concluded that each pigment is responsible for the petal’s colors and the compositions of the pigments affect their flower colors and that the cultivars could be a good source for pharmaceutical, floriculture, and pigment industries.

  6. Alternative natural dyes in water purification: Anthocyanin as TiO 2-sensitizer in methyl orange photo-degradation

    Zyoud, Ahed; Zaatar, Nidal; Saadeddin, Iyad; Helal, Muath H.; Campet, Guy; Hakim, Moulki; Park, DaeHoon; Hilal, Hikmat S.

    2011-06-01

    Natural molecular dye, anthocyanin, is described here as safe sensitizer for TiO 2 particles in photo-degradation of organic contaminants in water. The dye is a promising replacement for the more costly and hazardous heavy metal based systems, such as CdS particles and Ru-compounds. TiO 2/anthocyanin effectively catalyzed the photo-degradation of methyl orange contaminant under solar simulator radiation. The new TiO 2/anthocyanin catalyst showed comparable efficiency to earlier systems, while avoiding their hazardous nature. When supported onto activated carbon (AC) particles, the resulting AC/TiO 2/anthocyanin system showed enhanced efficiency and ease of recovery from the catalytic reaction mixture. The natural dye molecules showed the tendency to degrade under photo-degradation conditions, just like earlier hazardous sensitizers. However, complete mineralization of anthocyanin occurred leaving no traces of organic species in solution. Sensitizer degradation caused deactivation of the supported catalyst on recovery. Such a shortcoming was overcome by re-treatment of the recovered catalysts with fresh dye. Effects of different reaction parameters on the catalyst efficiency were studied. A mechanism, similar to earlier CdS-sensitized catalyst systems, is proposed for the TiO 2/anthocyanin catalyst.

  7. Effect of floral cluster pruning on anthocyanin levels and anthocyanain-related gene expression in 'Houman' grape.

    Zhang, Lei; Xu, Yan-Shuai; Jia, Yue; Wang, Ji-Yuan; Yuan, Yue; Yu, Yang; Tao, Jian-Min

    2016-01-01

    Lateral floral clusters were removed from the main axis of the floral clusters of 'Houman' grape plants, leaving only 3-5-cm-long region of flowers at the end of the central axis. The floral clusters were pruned at 7 days prior to flowering. The effect of the pruning on fruit quality was assessed by determining the composition and levels of anthocyanins in the fruit and anthocyanin-related gene expression. Results indicated that floral cluster pruning significantly improved the quality of the fruit by increasing berry size, fruit weight and the total content of soluble solids. Floral cluster pruning also decreased the level of titratable acidity. Sixteen different anthocyanins were detected in fruit of the pruned clusters, while only 15 were detected in fruit from unpruned clusters. The level of anthocyanins was also significantly higher in fruit of the pruned clusters than in the unpruned clusters. Anthocyanin-related gene expression was also significantly upregulated to a higher level in fruit from pruned floral clusters as compared with unpruned clusters. The upregulation was closely associated with increases in anthocyanin biosynthesis. PMID:27555920

  8. Effect of floral cluster pruning on anthocyanin levels and anthocyanain-related gene expression in ‘Houman’ grape

    Zhang, Lei; Xu, Yan-shuai; Jia, Yue; Wang, Ji-yuan; Yuan, Yue; Yu, Yang; Tao, Jian-min

    2016-01-01

    Lateral floral clusters were removed from the main axis of the floral clusters of ‘Houman’ grape plants, leaving only 3–5-cm-long region of flowers at the end of the central axis. The floral clusters were pruned at 7 days prior to flowering. The effect of the pruning on fruit quality was assessed by determining the composition and levels of anthocyanins in the fruit and anthocyanin-related gene expression. Results indicated that floral cluster pruning significantly improved the quality of the fruit by increasing berry size, fruit weight and the total content of soluble solids. Floral cluster pruning also decreased the level of titratable acidity. Sixteen different anthocyanins were detected in fruit of the pruned clusters, while only 15 were detected in fruit from unpruned clusters. The level of anthocyanins was also significantly higher in fruit of the pruned clusters than in the unpruned clusters. Anthocyanin-related gene expression was also significantly upregulated to a higher level in fruit from pruned floral clusters as compared with unpruned clusters. The upregulation was closely associated with increases in anthocyanin biosynthesis. PMID:27555920

  9. The COI1 and DFR Genes are Essential for Regulation of Jasmonate-Induced Anthocyanin Accumulation in Arabidopsis

    Qin-Fang Chen; Liang-Ying Dai; Shi Xiao; Yun-Sheng Wang; Xiong-Lun Liu; Guo-Liang Wang

    2007-01-01

    Jasmonates (JAs) are a class of plant hormones that play important roles in the regulation of plant development and plant defense. It has been shown that Arabidopsis plants produce much higher levels of anthocyanins when treated exogenously with methyl jasmonate (MeJA). However, a molecular link between the JA response and anthocyanin production has not been determined. The CORONATINE INSENTITIVE1 (COI1) gene is a key player in the regulation of many JA-related responses. In the present study, we demonstrate that the COI1 gene is also required for the JA-induced accumulation of anthocyanins in Arabidopsis. Furthermore, the MeJA-inducible expression of DIHYDROFLA VONOL REDUCTASE (DFR), an essential component in the anthocyanin biosynthesis pathway, was completely eliminated in the coi1 mutant. Jasmonateinduced anthocyanin accumulation was found to be independent of auxin signaling. The present results indicate that the expression of both COI1 and DFR genes is required for the regulation of JA-induced anthocyanin accumulation and that DFR may be a key downstream regulator for this process.

  10. Effects of Anthocyanins on CAG Repeat Instability and Behaviour in Huntington’s Disease R6/1 Mice

    Møllersen, Linda; Moldestad, Olve; Rowe, Alexander D.; Bjølgerud, Anja; Holm, Ingunn; Tveterås, Linda; Klungland, Arne; Retterstøl, Lars

    2016-01-01

    Background: Huntington’s disease (HD) is a progressive neurodegenerative disorder caused by CAG repeat expansions in the HTT gene. Somatic repeat expansion in the R6/1 mouse model of HD depends on mismatch repair and is worsened by base excision repair initiated by the 7,8-dihydroxy-8-oxoguanine-DNA glycosylase (Ogg1) or Nei-like 1 (Neil1). Ogg1 and Neil1 repairs common oxidative lesions. Methods: We investigated whether anthocyanin antioxidants added daily to the drinking water could affect CAG repeat instability in several organs and behaviour in R6/1 HD mice. In addition, anthocyanin-treated and untreated R6/1 HD mice at 22 weeks of age were tested in the open field test and on the rotarod. Results: Anthocyanin-treated R6/1 HD mice showed reduced instability index in the ears and in the cortex compared to untreated R6/1 mice, and no difference in liver and kidney. There were no significant differences in any of the parameters tested in the behavioural tests among anthocyanin-treated and untreated R6/1 HD mice. Conclusions: Our results indicate that continuous anthocyanin-treatment may have modest effects on CAG repeat instability in the ears and the cortex of R6/1 mice. More studies are required to investigate if anthocyanin-treatment could affect behaviour earlier in the disease course. PMID:27540492

  11. Measurement of total anthocyanins content in flowering tea using near infrared spectroscopy combined with ant colony optimization models.

    Xiaowei, Huang; Xiaobo, Zou; Jiewen, Zhao; Jiyong, Shi; Xiaolei, Zhang; Holmes, Mel

    2014-12-01

    Flowering tea has become a popular beverage consumed across the world. Anthocyanins content is considered as an important quality index of flowering tea. The feasibility of using near infrared (NIR) spectra at the wavelength range of 10,000-4000 cm(-1) for rapid and nondestructive determination of total anthocyanins content in flowering tea was investigated. Ant colony optimization interval partial least squares (ACO-iPLS) and Genetic algorithm interval partial least squares (GA-iPLS) were used to develop calibration models for total anthocyanins content. Two characteristic wavelength regions (4590-4783, 5770-5,963 cm(-1)), which corresponding to the ultraviolet/visible absorption bands of anthocyanins, were selected by ACO-iPLS. The optimal ACO-iPLS model for total anthocyanins content (R=0.9856, RMSECV=0.1,198 mg/g) had better performance than full-spectrum PLS, iPLS, and GA-iPLS models. It could be concluded that NIR spectroscopy has significant potential in the nondestructive determination of total anthocyanins content in flowering tea. PMID:24996367

  12. Expression and Anthocyanin Biosynthesis-Modulating Potential of Sweet Cherry (Prunus avium L. MYB10 and bHLH Genes.

    Pavel Starkevič

    Full Text Available Anthocyanins are essential contributors to fruit coloration, an important quality feature and a breed determining trait of a sweet cherry fruit. It is well established that the biosynthesis of anthocyanins is regulated by an interplay of specific transcription factors belonging to MYB and bHLH families accompanied by a WD40 protein. In this study, we isolated and analyzed PaWD40, PabHLH3, PabHLH33, and several closely related MYB10 gene variants from different cultivars of sweet cherry, analyzed their expression in fruits with different anthocyanin levels at several developmental stages, and determined their capabilities to modulate anthocyanin synthesis in leaves of two Nicotiana species. Our results indicate that transcription level of variant PaMYB10.1-1 correlates with fruit coloration, but anthocyanin synthesis in Nicotiana was induced by another variant, PaMYB10.1-3, which is moderately expressed in fruits. The analysis of two fruit-expressed bHLH genes revealed that PabHLH3 enhances MYB-induced anthocyanin synthesis, whereas PabHLH33 has strong inhibitory properties.

  13. Expression and Anthocyanin Biosynthesis-Modulating Potential of Sweet Cherry (Prunus avium L.) MYB10 and bHLH Genes.

    Starkevič, Pavel; Paukštytė, Jurgita; Kazanavičiūtė, Vaiva; Denkovskienė, Erna; Stanys, Vidmantas; Bendokas, Vidmantas; Šikšnianas, Tadeušas; Ražanskienė, Aušra; Ražanskas, Raimundas

    2015-01-01

    Anthocyanins are essential contributors to fruit coloration, an important quality feature and a breed determining trait of a sweet cherry fruit. It is well established that the biosynthesis of anthocyanins is regulated by an interplay of specific transcription factors belonging to MYB and bHLH families accompanied by a WD40 protein. In this study, we isolated and analyzed PaWD40, PabHLH3, PabHLH33, and several closely related MYB10 gene variants from different cultivars of sweet cherry, analyzed their expression in fruits with different anthocyanin levels at several developmental stages, and determined their capabilities to modulate anthocyanin synthesis in leaves of two Nicotiana species. Our results indicate that transcription level of variant PaMYB10.1-1 correlates with fruit coloration, but anthocyanin synthesis in Nicotiana was induced by another variant, PaMYB10.1-3, which is moderately expressed in fruits. The analysis of two fruit-expressed bHLH genes revealed that PabHLH3 enhances MYB-induced anthocyanin synthesis, whereas PabHLH33 has strong inhibitory properties. PMID:25978735

  14. Evaluation of Antiproliferative Activity of Red Sorghum Bran Anthocyanin on a Human Breast Cancer Cell Line (MCF-7)

    Breast cancer is a leading cause of death in women worldwide both in the developed and developing countries. Thus effective treatment of breast cancer with potential antitumour drugs is important. In this paper, human breast cancer cell line MCF-7 has been employed to evaluate the antiproliferative activity of red sorghum bran anthocyanin. The present investigation showed that red sorghum bran anthocyanin induced growth inhibition of MCF-7 cells at significant level. The growth inhibition is dose dependent and irreversible in nature. When MCF-7 cells were treated with red sorghum bran anthocyanins due to activity of anthocyanin morphological changes were observed. The morphological changes were identified through the formation of apoptopic bodies. The fragmentation by these anthocyanins on DNA to oligonuleosomal-sized fragments, is a characteristic of apoptosis, and it was observed as concentration-dependent. Thus, this paper clearly demonstrates that human breast cancer cell MCF-7 is highly responsive by red sorghum bran anthocyanins result from the induction of apoptosis in MCF-7 cells.

  15. Influences of organically and conventionally grown strawberry cultivars on anthocyanins content and color in purees and low-sugar jams.

    Bursać Kovačević, Danijela; Putnik, Predrag; Dragović-Uzelac, Verica; Vahčić, Nada; Babojelić, Martina Skendrović; Levaj, Branka

    2015-08-15

    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. PMID:25794726

  16. Influence of Accelerated Solvent Extraction and Ultrasound-Assisted Extraction on the Anthocyanin Profile of Different Vaccinium Species in the Context of Statistical Models for Authentication.

    Heffels, Peter; Weber, Fabian; Schieber, Andreas

    2015-09-01

    Anthocyanins are frequently discussed as marker compounds for fruit product authenticity. Proper analysis including sample preparation for the determination of anthocyanin concentrations is crucial for the comparability of authenticity data. The present study determined the influence of accelerated solvent extraction (ASE) and ultrasound-assisted extraction (UAE), using two different solvent compositions on the anthocyanin profile of bilberries (Vaccinium myrtillus L.), lowbush blueberries (Vaccinium angustifolium Ait.), and American cranberries (Vaccinium macrocarpon Ait.). Besides differences in total anthocyanin concentrations in the extracts, significant deviations (p ≤ 0.05) in the individual anthocyanin concentration were observed, resulting in differing anthocyanin proportions. Linear discriminant analysis comparing the differences caused by the extraction method to the natural differences within a set of 26 bilberry and lowbush blueberry samples of different origins was conducted. It revealed that profile variations induced by the extraction methods are in a similar scale to profile variations as a result of geographic and climatic differences. PMID:26330254

  17. Exploitation of the complexation reaction of ortho-dihydroxylated anthocyanins with aluminum(III) for their quantitative spectrophotometric determination in edible sources.

    Bernal, Freddy A; Orduz-Diaz, Luisa L; Coy-Barrera, Ericsson

    2015-10-15

    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 (RSDlaw 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. PMID:25952844

  18. Betalain production is possible in anthocyanin-producing plant species given the presence of DOPA-dioxygenase and L-DOPA

    Harris Nilangani N; Javellana John; Davies Kevin M; Lewis David H; Jameson Paula E; Deroles Simon C; Calcott Kate E; Gould Kevin S; Schwinn Kathy E

    2012-01-01

    Abstract Background Carotenoids and anthocyanins are the predominant non-chlorophyll pigments in plants. However, certain families within the order Caryophyllales produce another class of pigments, the betalains, instead of anthocyanins. The occurrence of betalains and anthocyanins is mutually exclusive. Betalains are divided into two classes, the betaxanthins and betacyanins, which produce yellow to orange or violet colours, respectively. In this article we show betalain production in specie...

  19. Long-chain acyl-homoserine lactones from Methylobacterium mesophilicum: synthesis and absolute configuration.

    Pomini, Armando M; Cruz, Pedro L R; Gai, Cláudia; Araújo, Welington L; Marsaioli, Anita J

    2009-12-01

    The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity. PMID:19919062

  20. Ring-opening metathesis polymerization-based recyclable magnetic acylation reagents.

    Kainz, Quirin M; Linhardt, Roland; Maity, Pradip K; Hanson, Paul R; Reiser, Oliver

    2013-04-01

    An operationally simple method for the acylation of amines utilizing carbon-coated metal nanoparticles as recyclable supports is reported. Highly magnetic carbon-coated cobalt (Co/C) and iron (Fe/C) nanobeads were functionalized with a norbornene tag (Nb-tag) through a "click" reaction followed by surface activation employing Grubbs-II catalyst and subsequent grafting of acylated N-hydroxysuccinimide ROMPgels (ROMP=ring-opening metathesis polymerization). The high loading (up to 2.6 mmolg(-1) ) hybrid material was applied in the acylation of various primary and secondary amines. The products were isolated in high yields (86-99%) and excellent purities (all >95 % by NMR spectroscopy) after rapid magnetic decantation and simple evaporation of the solvents. The spent resins were successfully re-acylated by acid chlorides, anhydrides, and carboxylic acids and reused for up to five consecutive cycles without considerable loss of activity. PMID:23427021

  1. Eradication of Helicobacter pylori increases childhood growth and serum acylated ghrelin levels

    Yang, Yao-Jong; Sheu, Bor-Shyang; Yang, Hsiao-Bai; Lu, Cheng-Chan; Chuang, Ching-Chun

    2012-01-01

    AIM: To determine whether Helicobacter pylori (H. pylori)-infected children have reduced body weight (BW) and height (BH) growth, and if H. pylori eradication may restore growth while improving serum acylated ghrelin.

  2. Selective Acylation Enhances Membrane Charge Sensitivity of the Antimicrobial Peptide Mastoparan-X

    Etzerodt, Thomas Povl; Henriksen, Jonas Rosager; Rasmussen, Palle;

    2011-01-01

    The partitioning of the wasp venom peptide mastoparan-X (MPX) into neutral and negatively charged lipid membranes has been compared with two new synthetic analogs of MPX where the Nα-terminal of MPX was acylated with propanoic acid (PA) and octanoic acid (OA). The acylation caused a considerable...... change in the membrane partitioning properties of MPX and it was found that the shorter acylation with PA gave improved affinity and selectivity toward negatively charged membranes, whereas OA decreased the selectivity. Based on these findings, we hypothesize that minor differences in the embedding and...... positioning of the peptide in the membrane caused by either PA or OA acylation play a critical role in the fine-tuning of the effective charge of the peptide and thereby the fine-tuning of the peptide's selectivity between neutral and negatively charged lipid membranes. This finding is unique compared to...

  3. Anthocyanins, phenolics and antioxidant capacity after fresh storage of blueberry treated with edible coatings.

    Chiabrando, Valentina; Giacalone, Giovanna

    2015-05-01

    The influence of different edible coatings on total phenolic content, total anthocyanin and antioxidant capacity in highbush blueberry (Vaccinium corymbosum L. cv Berkeley and O'Neal) was investigated, mainly for industrial applications. Also titratable acidity, soluble solids content, firmness and weight loss of berries were determined at harvest and at 15-day intervals during 45 storage days at 0 °C, in order to optimize coating composition. Application of chitosan coating delayed the decrease in anthocyanin content, phenolic content and antioxidant capacity. Coating samples showed no significant reduction in the weight loss during storage period. In cv Berkeley, the use of alginate coating showed a positive effect on firmness, titratable acidity and maintained surface lightness of treated berries. In cv O'Neal, no significant differences in total soluble solids content were found, and the chitosan-coated berries showed the minimum firmness losses. In both cultivars, the addition of chitosan to coatings decreases the microbial growth rate. PMID:25666416

  4. Bioavailability studies and anticancer properties of malvidin based anthocyanins, pyranoanthocyanins and non-oxonium derivatives.

    Oliveira, Hélder; Wu, Nao; Zhang, Qian; Wang, Jingyi; Oliveira, Joana; de Freitas, Victor; Mateus, Nuno; He, Jingren; Fernandes, Iva

    2016-05-18

    In this study, the gastric transport efficiency of malvidin-3-glucoside and several derivatives was assayed on the MKN-28 cell model. The transport efficiency was found to increase for all compounds with the incubation time. Pyranoanthocyanins may slightly impair transport efficiency levels in comparison with native anthocyanins. Among the pyranoanthocyanin derivatives the presence of the carbonyl group and the absence of charge were important for the transport efficiency percentage of oxovitisin and apparently compensated the negative effect associated with the additional ring. Moreover, the antiproliferative properties of these compounds in the MCF-7 cancer cell line were assayed, oxovitisin being the most effective compound in inhibiting the proliferation of MCF-7 cells. Also, a kinetic incorporation of oxovitisin was assayed revealing that this pyranoanthocyanin is quickly incorporated into cells. This study confirms the importance of the natural micro-oxidative processes that occur during the ageing of anthocyanin-containing food and their impact on their bioavailability and bioactivity properties. PMID:27165855

  5. Evaluation of the pH and thermal stabilities of rosella anthocyanin extracts under solar light

    Kahtan A. Askar

    2015-09-01

    Full Text Available Anthocyanin is considered as an unstable pigment, undergoes gradual degradation processes throughout the storage or use. The degradation of Rosella anthocyanin extract (RAE in different pH solutions was studied under solar light and compared with solutions kept in the dark. It appears that RAE solutions under solar light were suffering rapid degradation than those kept in the dark. Moreover, RAE samples at higher pH values showed faster rates of degradation than those with lower pH values. A mechanism for degradation was suggested through the formation of hydroxyl radical which is responsible for demineralization process. It is also appears that as the initial concentration of the dye increases, the requirement needed for degradation increased as well. The thermal degradation behavior of RAE at temperature range 25–60 °C under solar light showed first order kinetics with low activation energies.

  6. Electronic structure and optical properties of some anthocyanins extracted from grapes

    Iosub, Ion; Kajzar, Francois; Makowska-Janusik, Malgorzata; Meghea, Aurelia; Tane, Alexandrina; Rau, Ileana

    2012-08-01

    The pallet of applications of natural dyes and pigments is continuously extending as a stringent need to meet the challenges arisen from sustainable development, particularly related to replacing synthetic chemicals by eco-friendly renewable raw materials. In this respect, the well known nutritive and therapeutic properties demonstrated by anthocyanin compounds present in selective plant extracts of numerous fruits, vegetables and flowers could be largely complemented by their characteristics as chromophores and fluorophores with high potential in promising applications in bio-imaging for diagnostic and therapy, but also in electronic and photonic devices, solar cells, etc. In this context, this paper proposes an improved protocol for extraction and HPLC detection of anthocyanins from black grapes. Moreover, in order to exploit their potential to be applied as chromatic and fluorescence molecular probes, the electronic properties have been studied by correlating spectral characteristics with trichromatic parameters, combined with quantum chemistry computation.

  7. Pressurized Hot Water Extraction of anthocyanins from red onion: A study on extraction and degradation rates

    Pressurized Hot Water Extraction (PHWE) is a quick, efficient and environmentally friendly technique for extractions. However, when using PHWE to extract thermally unstable analytes, extraction and degradation effects occur at the same time, and thereby compete. At first, the extraction effect dominates, but degradation effects soon take over. In this paper, extraction and degradation rates of anthocyanins from red onion were studied with experiments in a static batch reactor at 110 deg. C. A total extraction curve was calculated with data from the actual extraction and degradation curves, showing that more anthocyanins, 21-36% depending on the species, could be extracted if no degradation occurred, but then longer extraction times would be required than those needed to reach the peak level in the apparent extraction curves. The results give information about the different kinetic processes competing during an extraction procedure.

  8. Specificity of acyl-homoserine lactone synthases examined by mass spectrometry.

    Gould, Ty A; Herman, Jake; Krank, Jessica; Murphy, Robert C; Churchill, Mair E A

    2006-01-01

    Many gram-negative bacteria produce a specific set of N-acyl-L-homoserine-lactone (AHL) signaling molecules for the purpose of quorum sensing, which is a means of regulating coordinated gene expression in a cell-density-dependent manner. AHLs are produced from acylated acyl-carrier protein (acyl-ACP) and S-adenosyl-L-methionine by the AHL synthase enzyme. The appearance of specific AHLs is due in large part to the intrinsic specificity of the enzyme for subsets of acyl-ACP substrates. Structural studies of the Pantoea stewartii enzyme EsaI and AHL-sensitive bioassays revealed that threonine 140 in the acyl chain binding pocket directs the enzyme toward production of 3-oxo-homoserine lactones. Mass spectrometry was used to examine the range of AHL molecular species produced by AHL synthases under a variety of conditions. An AHL selective normal-phase chromatographic purification with addition of a deuterated AHL internal standard was followed by reverse-phase liquid chromatography-tandem mass spectrometry in order to obtain estimates of the relative amounts of different AHLs from biological samples. The AHLs produced by wild-type and engineered EsaI and LasI AHL synthases show that intrinsic specificity and different cellular conditions influence the production of AHLs. The threonine at position 140 in EsaI is important for the preference for 3-oxo-acyl-ACPs, but the role of the equivalent threonine in LasI is less clear. In addition, LasI expressed in Escherichia coli produces a high proportion of unusual AHLs with acyl chains consisting of an odd number of carbons. Furthermore, these studies offer additional methods that will be useful for surveying and quantitating AHLs from different sources. PMID:16385066

  9. LuxR homolog-independent gene regulation by acyl-homoserine lactones in Pseudomonas aeruginosa.

    Chugani, Sudha; Greenberg, Everett Peter

    2010-06-01

    Pseudomonas aeruginosa quorum control of gene expression involves three LuxR-type signal receptors LasR, RhlR, and QscR that respond to the LasI- and RhlI-generated acyl-homoserine lactone (acyl-HSL) signals 3OC12-HSL and C4-HSL. We found that a LasR-RhlR-QscR triple mutant responds to acyl-HSLs by regulating at least 37 genes. LuxR homolog-independent activation of the representative genes antA and catB also occurs in the wild type. Expression of antA was influenced the most by C10-HSL and to a lesser extent by other acyl-HSLs, including the P. aeruginosa 3OC12-HSL and C4-HSL signals. The ant and cat operons encode enzymes for the degradation of anthranilate to tricarboxylic acid cycle intermediates. Our results indicate that LuxR homolog-independent acyl-HSL control of the ant and cat operons occurs via regulation of antR, which codes for the transcriptional activator of the ant operon. Although P. aeruginosa has multiple pathways for anthranilate synthesis, one pathway-the kynurenine pathway for tryptophan degradation-is required for acyl-HSL activation of the ant operon. The kynurenine pathway is also the critical source of anthranilate for energy metabolism via the antABC gene products, as well as the source of anthranilate for synthesis of the P. aeruginosa quinolone signal. Our discovery of LuxR homolog-independent responses to acyl-HSLs provides insight into acyl-HSL signaling. PMID:20498077

  10. Pharmacokinetics of naproxen, its metabolite O-desmethylnaproxen, and their acyl glucuronides in humans.

    Vree, T B; van den Biggelaar-Martea, M; Verwey-van Wissen, C P; Vree, J B; Guelen, P J

    1993-08-01

    The aim of this investigation was to assess the pharmacokinetics of naproxen in 10 human subjects after an oral dose of 500 mg using a direct HPLC analysis of the acyl glucuronide conjugates of naproxen and its metabolite O-desmethylnaproxen. The mean t1/2 of naproxen in 9 subjects was 24.7 +/- 6.4 h (range 16 to 36 h). The t1/2 of 7.4 as found in subject number 10 must, therefore, be regarded as an extraordinary case (p < 0.0153). Naproxen acyl glucuronide accounts for 50.8 +/- 7.32 per cent of the dose, its isomerized conjugate isoglucuronide for 6.5 +/- 2.0 per cent, O-desmethylnaproxen acyl glucuronide for 14.3 +/- 3.4 per cent, and its isoglucuronide for 5.5 +/- 1.3 per cent (n = 10; 100 h collection period). Naproxen and O-desmethylnaproxen are excreted in negligible amounts (< 1 per cent). Even though urine pH of the subjects was kept acid (range pH 5.0-5.5) in order to stabilize the acyl glucuronides, isomerization takes place in blood when the acyl glucuronide is released from the liver for excretion by the kidney. Binding to plasma proteins was measured as 98 per cent and 100 per cent, respectively for the unconjugated compounds naproxen and O-desmethylnaproxen. Binding of the acyl glucuronides was less, being 92 per cent; for naproxen acyl glucuronide, 66 per cent for naproxen isoglucuronide, 72 per cent for O-desmethylnaproxen acyl glucuronide and 42 per cent for O-desmethylnaproxen isoglucuronide. PMID:8218967

  11. Inhibition of DNA–Topoisomerase I by Acylated Triterpene Saponins from Pittosporum angustifolium Lodd.

    Baecker, C; Drwal, M.N.; Preissner, R; Lindequist, U.

    2016-01-01

    Abstract Previous phytochemical investigation of the leaves and seeds of Pittosporum angustifolium Lodd. led to the isolation and structural elucidation of polyphenols and triterpene saponins. Evaluation for cytotoxicity of isolated saponins revealed that the predominant structural feature for a cytotoxic activity are acyl substituents at the oleanane aglycon backbone. The present work reports the results of a screening of 10 selected acylated saponins for their potential to inhibit the human...

  12. Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber

    Na Gao; Mingyi Wu; Shao Liu; Wu Lian; Zi Li; Jinhua Zhao

    2012-01-01

    Fucosylated chondroitin sulfate (FuCS), a kind of complex glycosaminoglycan from sea cucumber, has potent anticoagulant activity. In order to understand the relationship between structures and activity, the depolymerized FuCS (dFuCS) was chosen to prepare its derivates by selective substitution at OH groups. Its O-acylation was carried out in a homogeneous way using carboxylic acid anhydrides. The structures of O-acylated derivatives were characterize...

  13. Very long chain acyl-coenzyme A dehydrogenase deficiency with adult onset

    Smelt, A H; Poorthuis, B J; Onkenhout, W; Scholte, H R; Andresen, B S; van Duinen, S G; Gregersen, N; Wintzen, A R

    1998-01-01

    Very long chain acyl-coenzyme A (acyl-CoA) dehydrogenase (VLCAD) deficiency is a severe disorder of mitochondrial beta-oxidation in infants. We report adult onset of attacks of painful rhabdomyolysis. Gas chromatography identified strongly elevated levels of tetradecenoic acid, 14:1(n-9), tetrade...... be due to residual enzyme activity as a consequence of the two missense mutations. Treatment with L-carnitine and medium chain triglycerides in the diet did not reduce the attacks of rhabdomyolysis....

  14. Acyl Meldrum's acid derivatives: application in organic synthesis

    This review is focused on an important class of Meldrum's acid derivatives commonly known as acyl Meldrum's acids. The preparation methods of these compounds are considered including the recently proposed and rather rarely used ones. The chemical properties of acyl Meldrum's acids are described in detail, including thermal stability and reactions with various nucleophiles. The possible mechanisms of these transformations are analyzed. The bibliography includes 134 references

  15. The Acute Effects of Swimming on Appetite, Food Intake, and Plasma Acylated Ghrelin

    Stensel, David J.; Wasse, Lucy K.; King, James A

    2011-01-01

    Swimming may stimulate appetite and food intake but empirical data are lacking. This study examined appetite, food intake, and plasma acylated ghrelin responses to swimming. Fourteen healthy males completed a swimming trial and a control trial in a random order. Sixty min after breakfast participants swam for 60 min and then rested for six hours. Participants rested throughout the control trial. During trials appetite was measured at 30 min intervals and acylated ghrelin was assessed periodic...

  16. Anthocyanin Interactions with DNA: Intercalation, Topoisomerase I Inhibition and Oxidative Reactions

    Webb, Michael R.; Min, Kyungmi; Susan E. Ebeler

    2008-01-01

    Anthocyanins and their aglycone anthocyanidins are pigmented flavonoids found in significant amounts in many commonly consumed foods. They exhibit a complex chemistry in aqueous solution, which makes it difficult to study their chemistry under physiological conditions. Here we used a gel electrophoresis assay employing supercoiled DNA plasmid to examine the ability of these compounds (1) to intercalate DNA, (2) to inhibit human topoisomerase I through both inhibition of plasmid relaxation act...

  17. Light signaling induces anthocyanin biosynthesis via AN3 mediated COP1 expression

    Meng, Lai-Sheng; Liu, Aizhong

    2015-01-01

    Light signaling plays a pivotal role in controlling plant morphogenesis, metabolism, growth and development. The central process of light signaling pathway is to build the link between light signals and the expression of genes involved. Although studies focused on light signaling toward metabolism have been documented well in the past several decades, most regulation networks of light signaling in a specific metabolic production largely remained unknown. Anthocyanin accumulation in plant tiss...

  18. Red Chicory (Cichorium intybus L. cultivar) as a Potential Source of Antioxidant Anthocyanins for Intestinal Health

    Laura D'Evoli; Fabiana Morroni; Ginevra Lombardi-Boccia; Massimo Lucarini; Patrizia Hrelia; Giorgio Cantelli-Forti; Andrea Tarozzi

    2013-01-01

    Fruit- and vegetable-derived foods have become a very significant source of nutraceutical phytochemicals. Among vegetables, red chicory (Cichorium Intybus L. cultivar) has gained attention for its content of phenolic compounds, such as the anthocyanins. In this study, we evaluated the nutraceutical effects, in terms of antioxidant, cytoprotective, and antiproliferative activities, of extracts of the whole leaf or only the red part of the leaf of Treviso red chicory (a typical Italian red leaf...

  19. Anthocyanin-sensitized solar cells using carbon nanotube films as counter electrodes

    Zhu, Hongwei; Zeng, Haifeng; Subramanian, Venkatachalam; Masarapu, Charan; Hung, Kai-Hsuan; Wei, Bingqing

    2008-11-01

    Carbon nanotube (CNT) films have been used as counter electrodes in natural dye-sensitized (anthocyanin-sensitized) solar cells to improve the cell performance. Compared with conventional cells using natural dye electrolytes and platinum as the counter electrodes, cells with a single-walled nanotube (SWNT) film counter electrode show comparable conversion efficiency, which is attributed to the increase in short circuit current density due to the high conductivity of the SWNT film.

  20. Protective Effect of Anthocyanins from Lingonberry on Radiation-induced Damages

    Shuang-Qi Tian; Zhen-Yu Wang; Li-Li Zuo; Zi-Luan Fan

    2012-01-01

    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 e...

  1. Anthocyanin production as a potential visual selection marker during plant transformation

    Kortstee, A J; S.A. Khan; Helderman, C.M.; Trindade, L.M.; Wu, Y.; Visser, R. G. F.; Brendolise, C.; Allan, A.C.; Schouten, H J; Jacobsen, E.

    2011-01-01

    A mutant allele of the transcription factor gene MYB10 from apple induces anthocyanin production throughout the plant. This gene, including its upstream promoter, gene coding region and terminator sequence, was introduced into apple, strawberry and potato plants to determine whether it could be used as a visible selectable marker for plant transformation as an alternative to chemically selectable markers, such as kanamycin resistance. After transformation, red coloured calli, red shoots and r...

  2. Anthocyanin-sensitized solar cells using carbon nanotube films as counter electrodes

    Carbon nanotube (CNT) films have been used as counter electrodes in natural dye-sensitized (anthocyanin-sensitized) solar cells to improve the cell performance. Compared with conventional cells using natural dye electrolytes and platinum as the counter electrodes, cells with a single-walled nanotube (SWNT) film counter electrode show comparable conversion efficiency, which is attributed to the increase in short circuit current density due to the high conductivity of the SWNT film.

  3. A Genomic Approach to Study Anthocyanin Synthesis and Flower Pigmentation in Passionflowers

    Marcelo Carnier Dornelas; Lilian Cristina Baldon Aizza

    2011-01-01

    Most of the plant pigments ranging from red to purple colors belong to the anthocyanin group of flavonoids. The flowers of plants belonging to the genus Passiflora (passionflowers) show a wide range of floral adaptations to diverse pollinating agents, including variation in the pigmentation of floral parts ranging from white to red and purple colors. Exploring a database of expressed sequence tags obtained from flower buds of two divergent Passiflora species, we obtained assembled sequences p...

  4. Measurement of Antioxidant Activity of Wine Catechins, Procyanidins, Anthocyanins and Pyranoanthocyanins

    Julián C. Rivas-Gonzalo; Milan ŽemliÄÂka; María P. Martín-López; María García-Alonso; Jan Muselík

    2007-01-01

    Nowadays, there is considerable interest in finding out about antioxidants that are consumed in the habitual diet. It is known that polyphenols are involved in reducing the risk of diseases associated with oxidative stress. The in vitro antioxidant activity of the principal wine polyphenolic compounds (catechins, procyanidins, anthocyanins and pyranoanthocyanins) was studied in this work. Four distinct methods were used to assess the antioxidant capacity of the tested compounds: inhibition of...

  5. Anthocyanin profiles of Crataegus monogyna Jacq. fruits in different maturity stages

    Barreira, João C. M.; Rodrigues, Sandra; Dueñas, Montserrat; Carvalho, Ana Maria; Santos-Buelga, Celestino; Ferreira, Isabel C. F. R.

    2013-01-01

    The vast structural diversity of natural compounds found in plants provides unique opportunities for discovering new drugs. Anthocyanins are an example of bioactive compounds with possible beneficial effects on human health (/). Crataegus monogyna Jacq. (hawthorn) has been extensively studied due to its various alleged health benefits (2) . Herein, samples from fruits on three different maturity stages (unripe, ripened and over ripened fruits) were extracted with acidified (trifluoracetic ...

  6. Simple Rain-Shelter Cultivation Prolongs Accumulation Period of Anthocyanins in Wine Grape Berries

    Xiao-Xi Li; Fei He; Jun Wang; Zheng Li; Qiu-Hong Pan

    2014-01-01

    Simple rain-shelter cultivation is normally applied during the grape growth season in continental monsoon climates aiming to reduce the occurrence of diseases caused by excessive rainfall. However, whether or not this cultivation practice affects the composition and concentration of phenolic compounds in wine grapes remains unclear. The objective of this study was to investigate the effect of rain-shelter cultivation on the accumulation of anthocyanins in wine grapes (Vitis vinifera L. Cabern...

  7. Epidermal coumaroyl anthocyanins protect sweet basil against excess light stress: multiple consequences of light attenuation.

    Tattini, Massimiliano; Landi, Marco; Brunetti, Cecilia; Giordano, Cristiana; Remorini, Damiano; Gould, Kevin S; Guidi, Lucia

    2014-11-01

    The putative photoprotective role of foliar anthocyanins continues to attract heated debate. Strikingly different experimental set-ups coupled with a poor knowledge of anthocyanin identity have likely contributed to such disparate opinions. Here, the photosynthetic responses to 30 or 100% solar irradiance were compared in two cultivars of basil, the green-leafed Tigullio (TG) and the purple-leafed Red Rubin (RR). Coumaroyl anthocyanins in RR leaf epidermis significantly mitigated the effects of high light stress. In full sunlight, RR leaves displayed several shade-plant traits; they transferred less energy than did TG to photosystem II (PSII), and non-photochemical quenching was lower. The higher xanthophyll cycle activity in TG was insufficient to prevent inactivation of PSII in full sunlight. However, TG was the more efficient in the shade; RR was far less able to accommodate a large change in irradiance. Investment of carbon to phenylpropanoid biosynthesis was more in RR than in TG in the shade, and was either greatly enhanced in TG or varied little in RR because of high sunlight. The metabolic cost of photoprotection was lower whereas light-induced increase in biomass production was higher in RR than in TG, thus making purple basil the more light tolerant. Purple basil appears indeed to display the conservative resource-use strategy usually observed in highly stress tolerant species. We conclude that the presence of epidermal coumaroyl anthocyanins confers protective benefits under high light, but it is associated with a reduced plasticity to accommodate changing light fluxes as compared with green leaves. PMID:24684471

  8. Natural Variation in Petal Color in Lycoris longituba Revealed by Anthocyanin Components

    He, Qiuling; Shen, Ye; Wang, Mingxiu; Huang, Minren; Yang, Ruizhen; Zhu, Shuijin; WANG, LIANGSHENG; Xu, Yanjun; Wu, Rongling

    2011-01-01

    Lycoris longituba is one of the species belonging to the Amaryllidaceae family. Despite its limited distribution, endemic to central eastern China, this species displays an exceptionally wide diversity of flower colors from purple, red, orange, to yellow, in nature. We study the natural variation of floral color in L. longituba by testing the components of water-soluble vacuolar pigments – anthocyanins – in its petals using high-performance liquid chromatography coupled with photodiode array ...

  9. Molecular genetics of blood-fleshed peach reveals activation of anthocyanin biosynthesis by NAC transcription factors.

    Zhou, Hui; Lin-Wang, Kui; Wang, Huiliang; Gu, Chao; Dare, Andrew P; Espley, Richard V; He, Huaping; Allan, Andrew C; Han, Yuepeng

    2015-04-01

    Anthocyanin pigmentation is an important consumer trait in peach (Prunus persica). In this study, the genetic basis of the blood-flesh trait was investigated using the cultivar Dahongpao, which shows high levels of cyanidin-3-glucoside in the mesocarp. Elevation of anthocyanin levels in the flesh was correlated with the expression of an R2R3 MYB transcription factor, PpMYB10.1. However, PpMYB10.1 did not co-segregate with the blood-flesh trait. The blood-flesh trait was mapped to a 200-kb interval on peach linkage group (LG) 5. Within this interval, a gene encoding a NAC domain transcription factor (TF) was found to be highly up-regulated in blood-fleshed peaches when compared with non-red-fleshed peaches. This NAC TF, designated blood (BL), acts as a heterodimer with PpNAC1 which shows high levels of expression in fruit at late developmental stages. We show that the heterodimer of BL and PpNAC1 can activate the transcription of PpMYB10.1, resulting in anthocyanin pigmentation in tobacco. Furthermore, silencing the BL gene reduces anthocyanin pigmentation in blood-fleshed peaches. The transactivation activity of the BL-PpNAC1 heterodimer is repressed by a SQUAMOSA promoter-binding protein-like TF, PpSPL1. Low levels of PpMYB10.1 expression in fruit at early developmental stages is probably attributable to lower levels of expression of PpNAC1 plus the presence of high levels of repressors such as PpSPL1. We present a mechanism whereby BL is the key gene for the blood-flesh trait in peach via its activation of PpMYB10.1 in maturing fruit. Partner TFs such as basic helix-loop-helix proteins and NAC1 are required, as is the removal of transcriptional repressors. PMID:25688923

  10. Characterisation by liquid chromatography-electrospray tandem mass spectrometry of anthocyanins in extracts of Myrtus communis L. berries used for the preparation of myrtle liqueur.

    Montoro, Paola; Tuberoso, Carlo I G; Perrone, Angela; Piacente, Sonia; Cabras, Paolo; Pizza, Cosimo

    2006-04-21

    Anthocyanins in extracts of berries of Myrtus communis, prepared following a typical Sardinia myrtle liqueur recipe, were identified and quantified by HPLC coupled with electrospray/tandem mass spectrometry using, respectively, an ion trap and a triple quadrupole mass analyser. The fragmentation patterns of the anthocyanidins were dependent on the MS technique employed, and differed considerably from those previously reported. The anthocyanin profile of five anthocyanin glucosides and four anthocyanin arabinosides, the latter not previously identified in this specie, was specific for myrtle berry extracts. The quantitative compositions of extracts of myrtle berries derived from different geographical areas in Italy were compared. PMID:16376912

  11. Characterization of Anthocyanins in Perilla frutescens var. acuta Extract by Advanced UPLC-ESI-IT-TOF-MSn Method and Their Anticancer Bioactivity

    Yan-Kang He

    2015-05-01

    Full Text Available The anthocyanin extract from a domestic Perilla cultivar (Perilla frutescens var. acuta were isolated and characterized with high mass accuracy and multi-dimensional fragmentation by means of ultra-performance liquid chromatography (UPLC and electrospray ionization-ion trap-time of flight mass spectrometry analysis (ESI-IT-TOF-MSn. The new developed and applied LC-MS method focused on in-depth screening of anthocyanin compounds with similar structures which also provided a new approach of anthocyanin characterization without the use of external standards. Selective detection of interested anthocyanins was achieved utilizing extracted ion chromatogram (EIC analysis, while MSn spectra were recorded to allow identification of the anthocyanin based on characteristic fragmentation patterns. Seven anthocyanins including one feruloyl (Cyanidin 3-O-feruloylglucoside-5-O-glucoside, two caffeoyl (Cyanidin 3-O-caffeoylglucoside-5-O-glucoside, Cyanidin 3-O-caffeoylglucoside-5-O-malonylglucoside and four coumaroyl substituted anthocyanins (Cis-shisonin, Malonyl-cis-shisonin, Shisonin, and Malonyl-shisonin were identified. Annexin-V FITC/PI flow cytometric assay was performed to analyze the influence of anthocyanin extract of P. frutescens var. acuta on cell apoptosis. The results suggested that Perilla anthocyanins can induce Hela cell apoptosis by a dose dependent manner.

  12. Plant Anthocyanin Synthesis and Gene Regulation%植物花青素合成与基因调控

    马延蕊; 张金文; 梁慧光; 柳永强

    2012-01-01

    文章在阐述植物花青素生物化学合成的基础上,综述了植物花色素苷合成的基因调控及环境、激素化学物质等外在因子对花青素基因调控的影响。结果表明:在植物花青素代谢中,温度、光照、紫外线、施肥状况、激素水平等因素能诱发花青素合成的调节基因或反义基因的表达,从而诱导或抑制了花青素的合成。在调控基因中,一些对花青素合成的结构蛋白表达产生促进作用,一些则具有抑制效应。不同外在因子激活或抑制调控基因的种类与数量不同,因此,产生了不同的花青素组型或相同组型的不同配比,使植物器官表现不同的颜色。%This paper aims to explain the biochemistry of anthocyanin synthesis based on an overview of plant anthocyanin synthesis genes and environmental factors in the regulation of anthocyanin metabolism. The results show that: ① The metabolism of anthocyanins in plants is affected by the temperature, light, ultraviolet, fertilization status, hormone levels and other factors, which affect the military anthocyanin biosynthetic genes, and then induce or inhibit the synthesis of anthocyanins. ② In the regulation of genes, some of the structural genes of anthocyanin synthesis showed promoting effect, while others showed inhibitory effect. At different environ- mental conditions, the regulation of gene activation and inhibition of the amount of different regulatory genes that anthocyanin accumulation is different, and cause different colors of plant-organs production. ③ In different environmental factors or hor-mones induced to produce the same or different regulation of gene expression changes in regulatory genes, resulting in several different anthocyanins or anthocyanin ratio changes, so that the color of plant organs in different colors.

  13. Deciphering the acylation pattern of Yersinia enterocolitica lipid A.

    Mar Reinés

    Full Text Available Pathogenic bacteria may modify their surface to evade the host innate immune response. Yersinia enterocolitica modulates its lipopolysaccharide (LPS lipid A structure, and the key regulatory signal is temperature. At 21°C, lipid A is hexa-acylated and may be modified with aminoarabinose or palmitate. At 37°C, Y. enterocolitica expresses a tetra-acylated lipid A consistent with the 3'-O-deacylation of the molecule. In this work, by combining genetic and mass spectrometric analysis, we establish that Y. enterocolitica encodes a lipid A deacylase, LpxR, responsible for the lipid A structure observed at 37°C. Western blot analyses indicate that LpxR exhibits latency at 21°C, deacylation of lipid A is not observed despite the expression of LpxR in the membrane. Aminoarabinose-modified lipid A is involved in the latency. 3-D modelling, docking and site-directed mutagenesis experiments showed that LpxR D31 reduces the active site cavity volume so that aminoarabinose containing Kdo(2-lipid A cannot be accommodated and, therefore, not deacylated. Our data revealed that the expression of lpxR is negatively controlled by RovA and PhoPQ which are necessary for the lipid A modification with aminoarabinose. Next, we investigated the role of lipid A structural plasticity conferred by LpxR on the expression/function of Y. enterocolitica virulence factors. We present evidence that motility and invasion of eukaryotic cells were reduced in the lpxR mutant grown at 21°C. Mechanistically, our data revealed that the expressions of flhDC and rovA, regulators controlling the flagellar regulon and invasin respectively, were down-regulated in the mutant. In contrast, the levels of the virulence plasmid (pYV-encoded virulence factors Yops and YadA were not affected in the lpxR mutant. Finally, we establish that the low inflammatory response associated to Y. enterocolitica infections is the sum of the anti-inflammatory action exerted by pYV-encoded YopP and the

  14. Effects of ghrelin and des-acyl ghrelin on neurogenesis of the rat fetal spinal cord

    Expressions of the growth hormone secretagogue receptor (GHS-R) mRNA and its protein were confirmed in rat fetal spinal cord tissues by RT-PCR and immunohistochemistry. In vitro, over 3 nM ghrelin and des-acyl ghrelin induced significant proliferation of primary cultured cells from the fetal spinal cord. The proliferating cells were then double-stained using antibodies against the neuronal precursor marker, nestin, and the cell proliferation marker, 5-bromo-2'-deoxyuridine (BrdU), and the nestin-positive cells were also found to be co-stained with antibody against GHS-R. Furthermore, binding studies using [125I]des-acyl ghrelin indicated the presence of a specific binding site for des-acyl ghrelin, and confirmed that the binding was displaced with unlabeled des-acyl ghrelin or ghrelin. These results indicate that ghrelin and des-acyl ghrelin induce proliferation of neuronal precursor cells that is both dependent and independent of GHS-R, suggesting that both ghrelin and des-acyl ghrelin are involved in neurogenesis of the fetal spinal cord

  15. Lipopolysaccharides with acylation defects potentiate TLR4 signaling and shape T cell responses.

    Martirosyan, Anna; Ohne, Yoichiro; Degos, Clara; Gorvel, Laurent; Moriyón, Ignacio; Oh, Sangkon; Gorvel, Jean-Pierre

    2013-01-01

    Lipopolysaccharides or endotoxins are components of Gram-negative enterobacteria that cause septic shock in mammals. However, a LPS carrying hexa-acyl lipid A moieties is highly endotoxic compared to a tetra-acyl LPS and the latter has been considered as an antagonist of hexa-acyl LPS-mediated TLR4 signaling. We investigated the relationship between the structure and the function of bacterial LPS in the context of human and mouse dendritic cell activation. Strikingly, LPS with acylation defects were capable of triggering a strong and early TLR4-dependent DC activation, which in turn led to the activation of the proteasome machinery dampening the pro-inflammatory cytokine secretion. Upon activation with tetra-acyl LPS both mouse and human dendritic cells triggered CD4(+) T and CD8(+) T cell responses and, importantly, human myeloid dendritic cells favored the induction of regulatory T cells. Altogether, our data suggest that LPS acylation controlled by pathogenic bacteria might be an important strategy to subvert adaptive immunity. PMID:23390517

  16. Anion channels and the stimulation of anthocyanin accumulation by blue light in Arabidopsis seedlings

    Noh, B.; Spalding, E. P.; Evans, M. H. (Principal Investigator)

    1998-01-01

    Activation of anion channels by blue light begins within seconds of irradiation in seedlings and is related to the ensuing growth inhibition. 5-Nitro-2-(3-phenylpropylamino)-benzoic acid (NPPB) is a potent, selective, and reversible blocker of these anion channels in Arabidopsis thaliana. Here we show that 20 microM NPPB blocked 72% of the blue-light-induced accumulation of anthocyanin pigments in seedlings. Feeding biosynthetic intermediates to wild-type and tt5 seedlings provided evidence that NPPB prevented blue light from up-regulating one or more steps between and including phenylalanine ammonia lyase and chalcone isomerase. NPPB was found to have no significant effect on the blue-light-induced increase in transcript levels of PAL1, CHS, CHI, or DFR, which are genes that encode anthocyanin-biosynthetic enzymes. Immunoblots revealed that NPPB also did not inhibit the accumulation of the chalcone synthase, chalcone isomerase, or flavanone-3-hydroxylase proteins. This is in contrast to the reduced anthocyanin accumulation displayed by a mutant lacking the HY4 blue-light receptor, as hy4 displayed reduced expression of the above enzymes. Taken together, the data indicate that blue light acting through HY4 leads to an increase in the amount of biosynthetic enzymes but blue light must also act through a separate, anion-channel-dependent system to create a fully functional biosynthetic pathway.

  17. Quality assessment of 178 cultivars of plum regarding phenolic, anthocyanin and sugar content.

    Sahamishirazi, Samira; Moehring, Jens; Claupein, Wilhelm; Graeff-Hoenninger, Simone

    2017-01-01

    In this study assessment of total phenolic, individual anthocyanin and total sugar content (TSC) of wide range of plum cultivars was done in order to select cultivars with high health benefiting compounds for potential breeding purposes. Total phenolics varied between 38.45 and 841.50mg GAE 100g(-1) FW. Cyaniding-3-rutinoside, cyaniding-3- glucoside and its equivalents were identified in anthocyanin measurement by HPLC with different ranges. TSC differed between 9.63 and 29.47%. Besides, evaluation of the effect of cultivar and year on phenolic content of 23 randomly selected cultivars over two following years (2013 & 2014) showed significant effect of both factors on phenolic content of plum cultivars. Overall, cultivars "Cacaks Spaete" which had high amount of total phenolics with stability over time, as well as "Hohenheim breed 4894" as a cultivar which contained high amounts of total phenolics, anthocyanins and TSC were selected for further breeding purposes to provide high nutritional quality plum to consumers. PMID:27507527

  18. High concentrations of anthocyanins in genuine cherry-juice of old local Austrian Prunus avium varieties.

    Schüller, Elisabeth; Halbwirth, Heidi; Mikulic-Petkovsek, Maja; Slatnar, Ana; Veberic, Robert; Forneck, Astrid; Stich, Karl; Spornberger, Andreas

    2015-04-15

    Antioxidant activity and polyphenols were quantified in vapour-extracted juice of nine Austrian, partially endemic varieties of sweet cherry (Prunus avium): cv. 'Spätbraune von Purbach', cv. 'Early Rivers', cv. 'Joiser Einsiedekirsche', cv. 'Große Schwarze Knorpelkirsche' and four unidentified local varieties. Additionally the effect of storage was evaluated for six of the varieties. A variety showing the highest antioxidant capacity (9.64 μmol Trolox equivalents per mL), total polyphenols (2747 mg/L) and total cyanidins (1085 mg/L) was suitable for mechanical harvest and its juice did not show any losses of antioxidant capacity and total anthocyanin concentration during storage. The juice of cv. 'Große Schwarze Knorpelkirsche' had also high concentrations of total anthocyanins (873 mg/L), but showed substantial losses through storage. The local Austrian sweet cherry varieties from the Pannonian climate zone are particularly suitable for the production of processed products like cherry juice with high content of anthocyanins and polyphenols. PMID:25466109

  19. Total phenolic, anthocyanin contents and antioxidant capacity of selected elderberry (Sambucus canadensis L. accessions

    Mustafa Ozgen

    2010-01-01

    Full Text Available Fourteen purple-black American elderberry accessions (Sambucus canadensis L. obtained from various sites in midwestern USA and then grown at a single Ohio production site in USA were analyzed for their total phenolic (TP and total monomeric anthocyanin (TMA contents and for their antioxidant capacity by the ferric reducing antioxidant power (FRAP and DPPH radical scavenging assays. Total phenolic and anthocyanin contents were measured using the Folin-Ciocalteu reagent and the pH differential methods, respectively. Overall, the phytonutrient contents and antioxidant capacity of our elderberry accessions were similar to those typically reported for black raspberries, blackberries and other dark-fleshed small fruits. Variability among accessions was greatest for TMA content (CV 37.5%; individuals ranged nearly threefold from 1308 to 4004 μg cy3-GE/g on a fresh weight basis. Variation among accessions was also evident for TP, FRAP and DPPH values (CV 14.4, 21.7 and 26.8%, respectively. TP and TMA values were very highly correlated (r = 0.93, although individuals differed in the estimated proportion of total phenolics attributable to anthocyanins. Both TP and TMA also highly correlated to antioxidant capacity values (r = 0.70-0.85. Within this limited study of 14 accessions, variability for phytonutrient content and antioxidant capacity suggested the employment of wild germplasm within an elderberry improvement program to incorporate an array of superior horticultural, post-harvest or processing traits into new or existing cultivars with superior phytonutrient profiles.

  20. Anthocyanin composition of wild Colombian fruits and antioxidant capacity measurement by electron paramagnetic resonance spectroscopy.

    Santacruz, Liliana; Carriazo, José G; Almanza, Ovidio; Osorio, Coralia

    2012-02-15

    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. PMID:22242913

  1. Flavanols and Anthocyanins in Cardiovascular Health: A Review of Current Evidence

    Sonia de Pascual-Teresa

    2010-04-01

    Full Text Available Nowadays it is accepted that natural flavonoids present in fruits and plant-derived-foods are relevant, not only for technological reasons and organoleptic properties, but also because of their potential health-promoting effects, as suggested by the available experimental and epidemiological evidence. The beneficial biological effects of these food bioactives may be driven by two of their characteristic properties: their affinity for proteins and their antioxidant activity. Over the last 15 years, numerous publications have demonstrated that besides their in vitro antioxidant capacity, certain phenolic compounds, such as anthocyanins, catechins, proanthocyanidins, and other non coloured flavonoids, may regulate different signaling pathways involved in cell survival, growth and differentiation. In this review we will update the knowledge on the cardiovascular effects of anthocyanins, catechins and proanthocyanidins, as implied by the in vitro and clinical studies on these compounds. We also review the available information on the structure, distribution and bioavailability of flavanols (monomeric catechins and proanthocyanidins and anthocyanins, data necessary in order to understand their role in reducing risk factors and preventing cardiovascular health problems through different aspects of their bioefficacy on vascular parameters (platelet agregation, atherosclerosis, blood pressure, antioxidant status, inflammation-related markers, etc., myocardial conditions, and whole-body metabolism (serum biochemistry, lipid profile, highlighting the need for better-designed clinical studies to improve the current knowledge on the potential health benefits of these flavonoids to cardiovascular and metabolic health.

  2. Anthocyanin content in dried berry skins and wine produced from dried grapes

    PEÇULI ANISA

    2014-06-01

    Full Text Available Anthocyanin, are the substances which are biosynthesized in the grape skin, extracted during the maceration and vinification and which contribute in wine color. During the aging of wines these substances are converted in their derivates, contributing in wine quality. For this reasons in nowadays there is a big attention of studies in these components. Wines from two grapes variety, a French variety, Cabernet Sauvignon and the other an autochthonous variety of Albania Kallmet were observed. The role of drying in concentration of anthocyanin in skins berry and if this technique is reflected in wine produced from this dried grape, was studied. The results shown that the quantity of anthocyanins from dried skins varied from 136 mg/100gr fresh product to 468 mg/100gr. The dried skins had the higher quantity, but this result was more significant for Cabernet Sauvignon wine than Kallmet wine. Measurement of phenolic content showed no significant changes between wines from dried and non-dried grapes.

  3. Simple Rain-Shelter Cultivation Prolongs Accumulation Period of Anthocyanins in Wine Grape Berries

    Xiao-Xi Li

    2014-09-01

    Full Text Available Simple rain-shelter cultivation is normally applied during the grape growth season in continental monsoon climates aiming to reduce the occurrence of diseases caused by excessive rainfall. However, whether or not this cultivation practice affects the composition and concentration of phenolic compounds in wine grapes remains unclear. The objective of this study was to investigate the effect of rain-shelter cultivation on the accumulation of anthocyanins in wine grapes (Vitis vinifera L. Cabernet Sauvignon grown in eastern China. The results showed that rain-shelter cultivation, compared with the open-field, extended the period of rapid accumulation of sugar, increased the soluble solid content in the grape berries, and delayed the senescence of the green leaves at harvest. The concentrations of most anthocyanins were significantly enhanced in the rain-shelter cultivated grapes, and their content increases were closely correlated with the accumulation of sugar. However, the compositions of anthocyanins in the berries were not altered. Correspondingly, the expressions of VvF3'H, VvF3'5'H, and VvUFGT were greatly up-regulated and this rising trend appeared to continue until berry maturation. These results suggested that rain-shelter cultivation might help to improve the quality of wine grape berries by prolonging the life of functional leaves and hence increasing the assimilation products.

  4. Progress in Regulation of Anthocyanins%花青素苷调控研究进展

    樊荣辉; 黄敏玲

    2013-01-01

    Anthocyanins are main determinants of plant flower colors.In recent years,with rapid development of molecular bio-technology and research,the regulation mechanism of anthocyanins has become increasingly clear.In order to provide theoretical reference for flower color improving,this review describes regulation mechanism about biosynthesis of anthocyanins,modification of anthocyanidins,co-pigments,vacuole pH value,metal ions and transcription factors.%花青素苷是决定植物花色的主要色素.近年来,随着分子生物学技术的发展及研究的深入,花青素苷调控机理越来越清晰.该文主要论述了花青素苷生物合成、分子修饰、助色素、液泡pH值、金属离子、转录因子等调控机制,以期为花色改良提供理论参考.

  5. Endogenous N-acyl taurines regulate skin wound healing.

    Sasso, Oscar; Pontis, Silvia; Armirotti, Andrea; Cardinali, Giorgia; Kovacs, Daniela; Migliore, Marco; Summa, Maria; Moreno-Sanz, Guillermo; Picardo, Mauro; Piomelli, Daniele

    2016-07-26

    The intracellular serine amidase, fatty acid amide hydrolase (FAAH), degrades a heterogeneous family of lipid-derived bioactive molecules that include amides of long-chain fatty acids with taurine [N-acyl-taurines (NATs)]. The physiological functions of the NATs are unknown. Here we show that genetic or pharmacological disruption of FAAH activity accelerates skin wound healing in mice and stimulates motogenesis of human keratinocytes and differentiation of human fibroblasts in primary cultures. Using untargeted and targeted lipidomics strategies, we identify two long-chain saturated NATs-N-tetracosanoyl-taurine [NAT(24:0)] and N-eicosanoyl-taurine [NAT(20:0)]-as primary substrates for FAAH in mouse skin, and show that the levels of these substances sharply decrease at the margins of a freshly inflicted wound to increase again as healing begins. Additionally, we demonstrate that local administration of synthetic NATs accelerates wound closure in mice and stimulates repair-associated responses in primary cultures of human keratinocytes and fibroblasts, through a mechanism that involves tyrosine phosphorylation of the epidermal growth factor receptor and an increase in intracellular calcium levels, under the permissive control of transient receptor potential vanilloid-1 receptors. The results point to FAAH-regulated NAT signaling as an unprecedented lipid-based mechanism of wound-healing control in mammalian skin, which might be targeted for chronic wound therapy. PMID:27412859

  6. A Continuous Procedure Based on Column Chromatography to Purify Anthocyanins from Schisandra chinensis by a Macroporous Resin plus Gel Filtration Chromatography

    Daran Yue

    2016-02-01

    Full Text Available In our previous study, as natural food colorants and antioxidants, the color and content stabilities of Schisandra chinensis (S. chinensis anthocyanins were investigated. In this work, the purification process parameters of S. chinensis anthocyanins using a macroporous resin and gel filtration chromatography were evaluated. The optimized parameters of static adsorption and desorption were as follows. The selected resin is HPD-300 (nonpolar copolymer styrene type resin, and the anthocyanins adsorption saturation capacity of HPD-300 resin was 0.475 mg/g dry resin. Adsorption time was 4 h, and 0.517 mg/mL of S. chinensis anthocyanins was adsorbed on the resin column with a flow rate of 39 mL/h (3 BV/h. After adsorption, the anthocyanins were completely desorpted with 2.5 BV of 90% (v/v ethanol solution, and the desorption flow rate was 13 mL/h (1 BV/h. After purification by dynamic adsorption and desorption, the anthocyanins content in the effluent increased from 47.6 mg/g to 128.4 mg/g, the purity of anthocyanins increased six-fold from 5.08% to 30.43%, and the anthocyanins recovery was 96.5%. The major constituent of S. chinensis anthocyanins was isolated with Bio-Gel P2 gel filtration chromatography, and it was detected by liquid chromatography electrospray ionisation tandem mass spectrometry (LC-ESI-MS as cyanidin-3-O-xylosylrutinoside. Moreover, the antioxidant activities of S. chinensis anthocyanins were investigated. After purification using the HPD-300 resin, the antioxidant activities of anthocyanins were increased 1.2-fold (FRAP and 1.7-fold (ABTS.

  7. A Continuous Procedure Based on Column Chromatography to Purify Anthocyanins from Schisandra chinensis by a Macroporous Resin plus Gel Filtration Chromatography.

    Yue, Daran; Yang, Lei; Liu, Shouxin; Li, Jian; Li, Wei; Ma, Chunhui

    2016-01-01

    In our previous study, as natural food colorants and antioxidants, the color and content stabilities of Schisandra chinensis (S. chinensis) anthocyanins were investigated. In this work, the purification process parameters of S. chinensis anthocyanins using a macroporous resin and gel filtration chromatography were evaluated. The optimized parameters of static adsorption and desorption were as follows. The selected resin is HPD-300 (nonpolar copolymer styrene type resin), and the anthocyanins adsorption saturation capacity of HPD-300 resin was 0.475 mg/g dry resin. Adsorption time was 4 h, and 0.517 mg/mL of S. chinensis anthocyanins was adsorbed on the resin column with a flow rate of 39 mL/h (3 BV/h). After adsorption, the anthocyanins were completely desorpted with 2.5 BV of 90% (v/v) ethanol solution, and the desorption flow rate was 13 mL/h (1 BV/h). After purification by dynamic adsorption and desorption, the anthocyanins content in the effluent increased from 47.6 mg/g to 128.4 mg/g, the purity of anthocyanins increased six-fold from 5.08% to 30.43%, and the anthocyanins recovery was 96.5%. The major constituent of S. chinensis anthocyanins was isolated with Bio-Gel P2 gel filtration chromatography, and it was detected by liquid chromatography electrospray ionisation tandem mass spectrometry (LC-ESI-MS) as cyanidin-3-O-xylosylrutinoside. Moreover, the antioxidant activities of S. chinensis anthocyanins were investigated. After purification using the HPD-300 resin, the antioxidant activities of anthocyanins were increased 1.2-fold (FRAP) and 1.7-fold (ABTS). PMID:26861279

  8. Effect of heterologous expression of acyl-CoA-binding protein on acyl-CoA level and composition in yeast

    Mandrup, S; Jepsen, R; Skøtt, H; Rosendal, J; Højrup, P; Kristiansen, K; Knudsen, J

    1993-01-01

    We have expressed a bovine synthetic acyl-CoA-binding protein (ACBP) gene in yeast (Saccharomyces cerevisiae) under the control of the GAL1 promoter. The heterologously expressed bovine ACBP constituted up to 6.4% of total cellular protein and the processing was identical with that of native bovi...

  9. Investigation of the kinetics of acyl group exchange Pt. 8. Intramolecular general base catalysis of isotopic acyl exchange between 8-acetoquinolines and acetic-1-/sup 14/C acid

    Dutka, F.; Marton, A.F. (Hungarian Academy of Sciences, Budapest. Central Research Inst. for Physics)

    1982-11-03

    8-acetoxyquinolines undergo isotopic acyl group exchange with acetic-1-/sup 14/C acid by the effect of ring nitrogen atom acting as an intramolecular general base catalytic function. Rate constants and activation parameters suggest a reaction mechanism intracomplex in nature.

  10. Removal of the acyl donor residue allows the use of simple alkyl esters as acyl donors for the dynamic kinetic resolution of secondary alcohols

    Verzijl, Gerard K.M.; Vries, Johannes G. de; Broxterman, Quirinus B.

    2005-01-01

    The dynamic kinetic resolution of secondary alcohols using a lipase and a ruthenium catalyst required some improvements to make it suitable for its use in an industrial process. The use of p-chlorophenyl acetate as acyl donor is not desirable in view of the toxicity of the side product. We herein re

  11. Insight into Coenzyme A cofactor binding and the mechanism of acyl-transfer in an acylating aldehyde dehydrogenase from Clostridium phytofermentans.

    Tuck, Laura R; Altenbach, Kirsten; Ang, Thiau Fu; Crawshaw, Adam D; Campopiano, Dominic J; Clarke, David J; Marles-Wright, Jon

    2016-01-01

    The breakdown of fucose and rhamnose released from plant cell walls by the cellulolytic soil bacterium Clostridium phytofermentans produces toxic aldehyde intermediates. To enable growth on these carbon sources, the pathway for the breakdown of fucose and rhamnose is encapsulated within a bacterial microcompartment (BMC). These proteinaceous organelles sequester the toxic aldehyde intermediates and allow the efficient action of acylating aldehyde dehydrogenase enzymes to produce an acyl-CoA that is ultimately used in substrate-level phosphorylation to produce ATP. Here we analyse the kinetics of the aldehyde dehydrogenase enzyme from the fucose/rhamnose utilisation BMC with different short-chain fatty aldehydes and show that it has activity against substrates with up to six carbon atoms, with optimal activity against propionaldehyde. We have also determined the X-ray crystal structure of this enzyme in complex with CoA and show that the adenine nucleotide of this cofactor is bound in a distinct pocket to the same group in NAD(+). This work is the first report of the structure of CoA bound to an aldehyde dehydrogenase enzyme and our crystallographic model provides important insight into the differences within the active site that distinguish the acylating from non-acylating aldehyde dehydrogenase enzymes. PMID:26899032

  12. Evolution of acyl-ACP-thioesterases and β-ketoacyl-ACP-synthases revealed by protein-protein interactions

    Beld, Joris; Jillian L Blatti; Behnke, Craig; Mendez, Michael; Burkart, Michael D.

    2013-01-01

    The fatty acid synthase (FAS) is a conserved primary metabolic enzyme complex capable of tolerating cross-species engineering of domains for the development of modified and overproduced fatty acids. In eukaryotes, acyl-acyl carrier protein thioesterases (TEs) off-load mature cargo from the acyl carrier protein (ACP), and plants have developed TEs for short/medium-chain fatty acids. We showed that engineering plant TEs into the green microalga Chlamydomonas reinhardtii does not result in the p...

  13. Acyl-ACP thioesterases from Camelina sativa: Cloning, enzymatic characterization and implication in seed oil fatty acid composition.

    Rodríguez-Rodríguez, Manuel Fernando; Salas, Joaquín J.; Garcés Mancheño, Rafael; Martínez-Force, Enrique

    2014-01-01

    Acyl-acyl carrier protein (ACP) thioesterases are intraplastidial enzymes that terminate de novo fatty acid biosynthesis in the plastids of higher plants by hydrolyzing the thioester bond between ACP and the fatty acid synthesized. Free fatty acids are then esterified with coenzyme A prior to being incorporated into the glycerolipids synthesized through the eukaryotic pathway. Acyl-ACP thioesterases belong to the TE14 family of thioester-active enzymes and can be classified as FatAs and FatBs...

  14. Rapid acyl-homoserine lactone quorum signal biodegradation in diverse soils.

    Wang, Ya-Juan; Leadbetter, Jared Renton

    2005-03-01

    Signal degradation impacts all communications. Although acyl-homoserine lactone (acyl-HSL) quorum-sensing signals are known to be degraded by defined laboratory cultures, little is known about their stability in nature. Here, we show that acyl-HSLs are biodegraded in soils sampled from diverse U.S. sites and by termite hindgut contents. When amended to samples at physiologically relevant concentrations, 14C-labeled acyl-HSLs were mineralized to 14CO2 rapidly and, at most sites examined, without lag. A lag-free turf soil activity was characterized in further detail. Heating or irradiation of the soil prior to the addition of radiolabel abolished mineralization, whereas protein synthesis inhibitors did not. Mineralization exhibited an apparent Km of 1.5 microM acyl-HSL, ca. 1,000-fold lower than that reported for a purified acyl-HSL lactonase. Under optimal conditions, acyl-HSL degradation proceeded at a rate of 13.4 nmol x h(-1) x g of fresh weight soil(-1). Bioassays established that the final extent of signal inactivation was greater than for its full conversion to CO2 but that the two processes were well coupled kinetically. A most probable number of 4.6 x 10(5) cells . g of turf soil(-1) degraded physiologically relevant amounts of hexanoyl-[1-14C]HSL to 14CO2. It would take chemical lactonolysis months to match the level of signal decay achieved in days by the observed biological activity. Rapid decay might serve either to quiet signal cross talk that might otherwise occur between spatially separated microbial aggregates or as a full system reset. Depending on the context, biological signal decay might either promote or complicate cellular communications and the accuracy of population density-based controls on gene expression in species-rich ecosystems. PMID:15746331

  15. Protective actions of des-acylated ghrelin on brain injury and blood-brain barrier disruption after stroke in mice.

    Ku, Jacqueline M; Taher, Mohammadali; Chin, Kai Yee; Barsby, Tom; Austin, Victoria; Wong, Connie H Y; Andrews, Zane B; Spencer, Sarah J; Miller, Alyson A

    2016-09-01

    The major ghrelin forms, acylated ghrelin and des-acylated ghrelin, are novel gastrointestinal hormones. Moreover, emerging evidence indicates that these peptides may have other functions including neuro- and vaso-protection. Here, we investigated whether post-stroke treatment with acylated ghrelin or des-acylated ghrelin could improve functional and histological endpoints of stroke outcome in mice after transient middle cerebral artery occlusion (tMCAo). We found that des-acylated ghrelin (1 mg/kg) improved neurological and functional performance, reduced infarct and swelling, and decreased apoptosis. In addition, it reduced blood-brain barrier (BBB) disruption in vivo and attenuated the hyper-permeability of mouse cerebral microvascular endothelial cells after oxygen glucose deprivation and reoxygenation (OGD + RO). By contrast, acylated ghrelin (1 mg/kg or 5 mg/kg) had no significant effect on these endpoints of stroke outcome. Next we found that des-acylated ghrelin's vasoprotective actions were associated with increased expression of tight junction proteins (occludin and claudin-5), and decreased cell death. Moreover, it attenuated superoxide production, Nox activity and expression of 3-nitrotyrosine. Collectively, these results demonstrate that post-stroke treatment with des-acylated ghrelin, but not acylated ghrelin, protects against ischaemia/reperfusion-induced brain injury and swelling, and BBB disruption, by reducing oxidative and/or nitrosative damage. PMID:27303049

  16. Effects of pretreatments on anthocyanin composition, phenolics contents and antioxidant capacities during fermentation of hawthorn (Crataegus pinnatifida) drink.

    Liu, Suwen; Chang, Xuedong; Liu, Xiufeng; Shen, Zhanwei

    2016-12-01

    The effect of microwave and heat pretreatment on the content and composition of anthocyanins, phenolics, and the antioxidant capacity of hawthorn drink were studied. Nine anthocyanins were isolated by chromatographic separation from the Zirou hawthorn source and their structure identified using HPLC-DAD-ESI/MS analysis. Heat and microwave pretreatments had a significant impact on the relative contents of hawthorn anthocyanins, such as cyanidin-3-galactoside (82.9% and 76.9%, respectively) and cyanidin-3-glucoside (9.2% and 11.5%, respectively). Pretreatment had no significant effect on pH, total soluble solid or total acid. More anthocyanins remained after heat treatment than after microwaving (0.745mg/100mL), and were 52.4% higher than the control group after storage for 7days. The colour density of the heat treated group was higher than the control group (24.5%) after 12days of fermentation. The main antioxidant capacities of the hawthorn drinks came from total polyphenolics rather than total anthocyanins or total flavonoids. PMID:27374510

  17. Optimization of ultrasound-assisted extraction of anthocyanins from haskap berries (Lonicera caerulea L.) using Response Surface Methodology.

    Celli, Giovana Bonat; Ghanem, Amyl; Brooks, Marianne Su-Ling

    2015-11-01

    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. PMID:26186866

  18. Comparative study of anthocyanin and volatile compounds content of four varieties of Mexican roselle (Hibiscus sabdariffa L.) by multivariable analysis.

    Camelo-Méndez, G A; Ragazzo-Sánchez, J A; Jiménez-Aparicio, A R; Vanegas-Espinoza, P E; Paredes-López, O; Del Villar-Martínez, A A

    2013-09-01

    Anthocyanins are a group of water-soluble pigments that provide red, purple or blue color to the leaves, flowers, and fruits. In addition, benefits have been attributed to hypertension and cardiovascular diseases. This study compared the content of total anthocyanins and volatile compounds in aqueous and ethanolic extracts of four varieties of Mexican roselle, with different levels of pigmentation. The multivariable analysis of categorical data demonstrated that ethanol was the best solvent for the extraction of both anthocyanins and volatile compounds. The concentration of anthocyanin in pigmented varieties ranged from 17.3 to 32.2 mg of cyanidin 3-glucoside/g dry weight, while volatile compounds analysis showed that geraniol was the main compound in extracts from the four varieties. The principal component analysis (PCA) allowed description of results with 77.38% of variance establishing a clear grouping for each variety in addition to similarities among some of these varieties. These results were validated by the confusion matrix obtained in the classification by the factorial discriminate analysis (FDA); it can be useful for roselle varieties classification. Small differences in anthocyanin and volatile compounds content could be detected, and it may be of interest for the food industry in order to classify a new individual into one of several groups using different variables at once. PMID:23715788

  19. Antidiabetic and Synergistic Effects of Anthocyanin Fraction from Berberis integerrima Fruit on Streptozotocin-Induced Diabetic Rats Model

    Zahra Sabahi

    2016-03-01

    Full Text Available Diabetes mellitus is a complex endocrine disorder. There is a serious attempt to identify antidiabetic compounds from natural sources to use with other drugs for reduction of diabetes complications. Present study is based on the investigation of antihyperglycemic effect of anthocyanin fraction of Berberis integerrima Bunge (AFBI fruits on some physiological parameters (glucose level, glycogen content, and body weight in normal and streptozotocin-induced (STZ-induced diabetic rats and evaluation of synergic effect of this fraction with metformin and glibenclamide. Male Sprague dawley rats were divided into nine groups: healthy control group, diabetic control group, diabetic groups treated with anthocyanin fraction (200, 400 and 1000 mg/kg, respectively; diabetic groups treated with glibenclamide and metformin separately, diabetic groups treated with glibenclamide + anthocyanin fraction (1000 mg/kg, metformin + anthocyanin fraction (1000 mg/kg. Treatment of diabetic rats with AFBI (400, 1000mg/kg significantly decreased blood glucose as compared with control. Moreover, AFBI (400, 1000mg/kg significantly increased liver glycogen and body weight compared to control. Nevertheless, there were no synergistic effects between anthocyanin fraction and metformin or glibenclamide on blood glucose, liver glycogen, and body weight. The results of this study indicate that AFBI possesses hypoglycemic effects and may be considered for evaluation in future diabetes clinical studies.

  20. Use of Modified Phenolic Thyme Extracts (Thymus vulgaris with Reduced Polyphenol Oxidase Substrates as Anthocyanin Color and Stability Enhancing Agents

    Oscar Aguilar

    2015-12-01

    Full Text Available Residual enzymatic activity in certain foods, particularly of polyphenoloxidase (PPO, is responsible for the majority of anthocyanin degradation in food systems, causing also parallel losses of other relevant nutrients. The present work explored the feasibility of modifying phenolic profiles of thyme extracts, by use of chromatographic resins, to obtain phenolic extracts capable of enhancing anthocyanin colour and stability in the presence of PPO activity. Results indicated that pretreatment of thyme extracts with strong-anion exchange resins (SAE enhanced their copigmentation abilities with strawberry juice anthocyanins. Phenolic chromatographic profiles, by HPLC-PDA, also demonstrated that thyme extracts subjected to SAE treatments had significantly lower concentrations of certain phenolic compounds, but extracts retained their colour enhancing and anthocyanin stabilization capacities though copigmentation. Additional testing also indicated that SAE modified extract had a lower ability (73% decrease to serve as PPO substrate, when compared to the unmodified extract. Phenolic profile modification process, reported herein, could be potentially used to manufacture modified anthocyanin-copigmentation food and cosmetic additives for colour-stabilizing applications with lower secondary degradation reactions in matrixes that contain PPO activity.