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Sample records for udp-l-rhamnose anthocyanidin 3-o-glucoside

  1. Different inhibition mechanisms of gentisic acid and cyaniding-3-O-glucoside on polyphenoloxidase.

    Science.gov (United States)

    Zhou, Lei; Xiong, Zhiqiang; Liu, Wei; Zou, Liqiang

    2017-11-01

    Gentisic acid and cyanidin-3-O-glucoside are important bioactive polyphenols which are widely distributed in many fruits and cereals. In this work, kinetic study, spectral analysis and computational simulation were used to compare the inhibitory effects and inhibition mechanisms of gentisic acid and cyanidin-3-O-glucoside on mushroom polyphenoloxidase (PPO). The inhibitory effect of cyanidin-3-O-glucoside on PPO was much stronger than that of gentisic acid. Gentisic acid inhibited PPO in a reversible mixed-type manner while cyanidin-3-O-glucoside was an irreversible inhibitor. Gentisic acid and cyanidin-3-O-glucoside made the thermal inactivation of PPO easier, and induced apparent conformational changes of PPO. Compared with gentisic acid, cyanidin-3-O-glucoside had stronger effects on the thermal inactivation and conformation of PPO. Molecular docking results revealed gentisic acid bound to the active site of PPO by hydrogen bonding, π-π stacking and van der Waals forces. However, cyanidin-3-O-glucoside might irreversibly interact with the Met or Cys in PPO by covalent bonds. Copyright © 2017 Elsevier Ltd. All rights reserved.

  2. Biological activity of quercetin-3-O-glucoside, a known plant flavonoid.

    Science.gov (United States)

    Razavi, Seyed Mehdi; Zahri, Saber; Zarrini, Gholamreza; Nazemiyeh, Hossein; Mohammadi, Sariyeh

    2009-01-01

    Cytotoxic, phytotoxic, antimicrobial and antioxidant effects of quercetin 3-O-glucoside (Q3G) isolated by HPLC from aerial parts of Prangos ferulaceae was studied by MTT assay, lettuce germination assay, disk diffusion and DPPH method. Our results showed that Q3G exhibits high antioxidant effect with RC(50) of 22 microg/mL, it has low cytotoxicity and no antibacterial effects. Q3G exhibits high phytotoxic effect with IC(50) value of 282.7 microg/ml, as well. It is assumed that Q3G does not play a defense role in plants and it may act as an allelopatic agent.

  3. Chemical behavior of methylpyranomalvidin-3-O-glucoside in aqueous solution studied by NMR and UV-visible spectroscopy.

    Science.gov (United States)

    Oliveira, Joana; Petrov, Vesselin; Parola, A Jorge; Pina, Fernando; Azevedo, Joana; Teixeira, Natércia; Brás, Natércia F; Fernandes, Pedro A; Mateus, Nuno; Ramos, Maria João; de Freitas, Victor

    2011-02-17

    In the present work, the proton-transfer reactions of the methylpyranomalvidin-3-O-glucoside pigment in water with different pH values was studied by NMR and UV-visible spectroscopies. The results showed four equilibrium forms: the methylpyranomalvidin-3-O-glucoside cation, the neutral quinoidal base, the respective anionic quinoidal base, and a dianionic base unprotonated at the methyl group. According to the NMR data, it seems that for methylpyranomalvidin-3-O-glucoside besides the acid-base equilibrium between the pyranoflavylium cation and the neutral quinoidal base, a new species is formed at pD 4.88-6.10. This is corroborated by the appearance of a new set of signals in the NMR spectrum that may be assigned to the formation of hemiketal/cis-chalcone species to a small extent. The two ionization constants (pK(a1) and pK(a2)) obtained by both methods (NMR and UV-visible) for methylpyranomalvidin-3-O-glucoside are in agreement (pK(a1) = 5.17 ± 0.03; pK(a2) = 8.85 ± 0.08; and pK(a1) = 4.57 ± 0.07; pK(a2) = 8.23 ± 0.04 obtained by NMR and UV-visible spectroscopies, respectively). Moreover, the fully dianionic unprotonated form (at the methyl group) of the methylpyranomalvidin-3-O-glucoside is converted slowly into a new structure that displays a yellow color at basic pH. On the basis of the results obtained through LC-MS and NMR, the proposed structure was found to correspond to the flavonol syringetin-3-glucoside.

  4. Entropy-driven complex formation of malvidin-3- O-glucoside with common polyphenols in ethanol-water binary solutions

    Science.gov (United States)

    Kunsági-Máté, Sándor; Ortmann, Erika; Kollár, László; Nikfardjam, Martin Pour

    2008-09-01

    The complex formation of malvidin-3- O-glucoside with several polyphenols, the so-called "copigmentation" phenomenon, was studied in aqueous solutions. To simulate the copigmentation process during fermentation, the stability of the formed complexes was examined in dependence of the ethanol content of the aqueous solution. Results indicate that stronger and larger complexes are formed, when the ethanol content exceeds a critical margin of 8 vol.% However, the size of complexes of malvidin/procyanidin and malvidin/epicatechin is drastically reduced above this critical concentration. Fluorescence lifetime and solvent relaxation measurements give insight into the particular processes at molecular level and will help us comprehend the first important steps during winemaking in order to recommend an optimized winemaking technology to ensure extraordinary colour stability in red wines.

  5. 13C CPMAS NMR Studies of Anthocyanidins and their Glucosides

    International Nuclear Information System (INIS)

    Wolniak, M.; Wawer, I.

    2005-01-01

    Anthocyanins are responsible for red, purple or blue colours of flower petals and can be found in red or black fruits and berries. Many foods, especially red grapes and wines, aronia or blueberries contain large amounts of anthocyanins. Their health beneficial effects are related to antioxidant and radical scavenging properties. Structural analysis of anthocyanins by NMR are few, owing to the difficulty in obtaining analysable spectra for unstable, interconverting compounds, available in small amounts. Compounds studied by us were isolated from fruits and berries. 13 C CPMAS NMR spectra were recorded on a Bruker DSX-400 spectrometer for solid chlorides of: cyanidin, cyanidin 3-O-glucoside, cyanidin 3,5-O-diglucoside, pelargonidin and pelargonidin 3-O-glucoside. Dipolar dephased and short contact pulse sequences were used as an aid in the assignment of resonances in CPMAS spectra of solids. Inspection of the spectra indicates that anthocyanidins are in the form of flavylium (cationic) and not in form of the chalcone.: the resonance of C2 appears at ca. 160 ppm and C3 at ca. 135 ppm, whereas C ring opening produces C2 = O, for which chemical shift of ca. 180 ppm can be expected. A comparison of experimental (CPMAS) and predicted (GIAO DFT) shielding constants for cyanidin provided information about the orientation of OH groups, twist angle of aromatic ring B and the localization of the chloride anion.(author)

  6. Charge Transfer Dynamics of Highly Efficient Cyanidin-3-O- Glucoside Sensitizer for Dye-Sensitized Solar Cells

    International Nuclear Information System (INIS)

    Prima, E C; Yuliarto, B; Suyatman; Dipojono, H K

    2016-01-01

    This paper reports the novel efficiency achievement of black rice-based natural dye- sensitized solar cells. The higher dye concentration, the longer dye extraction as well as dye immersion onto a TiO 2 film, and the co-adsorption addition are key strategies for improved-cell performance compared to the highest previous achievement. The black rice dye containing 1.38 mM cyanidin-3-O-glucoside has been extracted without purification for 3 weeks at dark condition and room temperature. The anatase TiO 2 photoanode was dipped into dye solution within 4 days. Its electrode was firmly sealed to be a cell and was filled by I - /I 3 - electrolyte using vacuum technique. As a result, the overall solar-to-energy conversion efficiency was 1.49% at AM 1.5 illumination (100 mW.cm -2 ). The voltametric analysis has reported the interfacial electronic band edges of TiO 2 -Dye-Electrolyte. Furthermore, electrochemical impedance spectroscopy has shown the kinetic of interfacial electron transfer dynamics among TiO 2 -dye-electrolyte. The cell has the transfer resistance (Rt) of 12.5 ω, the recombination resistance (Rr) of 266.8 ω, effective electron diffusion coefficients (Dn) of 1.4 × 10 -3 cm 2 /s, Dye-TiO 2 effective electron transfer (τ d ) of 26.6 μs, effective diffusion length (L n )of 33.78 μm, chemical capacitance (C μ ) of 12.43 μF, and electron lifetime (τ n ) of 3.32 ms. (paper)

  7. Reactivity of Cork Extracts with (+)-Catechin and Malvidin-3-O-glucoside in Wine Model Solutions: Identification of a New Family of Ellagitannin-Derived Compounds (Corklins).

    Science.gov (United States)

    Azevedo, Joana; Fernandes, Ana; Oliveira, Joana; Brás, Natércia F; Reis, Sofia; Lopes, Paulo; Roseira, Isabel; Cabral, Miguel; Mateus, Nuno; de Freitas, Victor

    2017-10-04

    The aim of this study was to evaluate the reactivity of phenolic compounds extracted from cork stoppers to wine model solutions with two major wine components, namely, (+)-catechin and malvidin-3-O-glucoside. Besides the formation of some compounds already described in the literature, these reactions also yielded a new family of ellagitannin-derived compounds, named herein as corklins. This new family of compounds that were found to result from the interaction between ellagitannins in alcoholic solutions and (+)-catechin were structurally characterized by mass spectroscopy, nuclear magnetic resonance, and computational methods.

  8. Computational and in vitro insights on snake venom phospholipase A2 inhibitor of phytocompound ikshusterol3-O-glucoside of Clematis gouriana Roxb. ex DC.

    Science.gov (United States)

    Muthusamy, Karthikeyan; Chinnasamy, Sathishkumar; Nagarajan, Subbiah; Sivaraman, Thirunavukkarasu

    2017-12-14

    Ikshusterol3-O-glucoside was isolated from Clematis gouriana Roxb. ex DC. root. A structure of the isolated compound was determined on the basis of various spectroscopic interpretations (UV, NMR, FTIR, and GC-MS-EI). This structure was submitted in the PubChem compound database (SID 249494133). SID 249494133 was carried out by density functional theory calculation to observe the chemical stability and electrostatic potential of this compound. The absorption, distribution, metabolism, and excretion property of this compound was predicted to evaluate the drug likeness and toxicity. In addition, molecular docking, quantum polarized ligand docking, prime MMGBSA calculation, and induced fit docking were performed to predict the binding status of SID 249494133 with the active site of phospholipase A 2 (PLA 2 ) (PDB ID: 1A3D). The stability of the compound in the active site of PLA 2 was carried out using molecular dynamics simulation. Further, the anti-venom activity of the compound was assessed using the PLA 2 assay against Naja naja (Indian cobra) crude venom. The results strongly show that Ikshusterol3-O-glucoside has a potent snake-venom neutralizing capacity and it might be a potential molecule for the therapeutic treatment for snakebites.

  9. Anthocyanins standards (cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside isolation from freeze-dried açaí (Euterpe oleraceae Mart. by HPLC

    Directory of Open Access Journals (Sweden)

    Ana Cristina Miranda Senna Gouvêa

    2012-03-01

    Full Text Available Availability of analytical standards is a critical aspect in developing methods for quantitative analysis of anthocyanins. The anthocyanins cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside were isolated from samples of freeze-dried açaí (Euterpe oleraceae Mart., which is a round and purple well-known palm fruit in Brazil, and then used as standards. The isolation of the anthocyanins was performed by High Performance Liquid Chromatography (HPLC, using an adapted six-channel selection valve. The identification of anthocyanin pigments in açaí was based on mass spectrometric data for molecular ions and MS-MS product ions and on previous published data. After the collection procedure, standards with a high purity grade were obtained and an external standard curve of each anthocyanin was plotted.

  10. Separation of patuletin-3-O-glucoside, astragalin, quercetin, kaempferol and isorhamnetin from Flaveria bidentis (L.) Kuntze by elution-pump-out high-performance counter-current chromatography.

    Science.gov (United States)

    Wei, Yun; Xie, Qianqian; Fisher, Derek; Sutherland, Ian A

    2011-09-09

    Flaveria bidentis (L.) Kuntze is an annual alien weed of Flaveria Juss. (Asteraceae) in China. Bioactive compounds, mainly flavonol glycosides and flavones from F. bidentis (L.) Kuntze, have been studied in order to utilize this invasive weed, Analytical high-performance counter-current chromatography (HPCCC) was successfully used to separate patuletin-3-O-glucoside, a mixture of hyperoside (quercetin-3-O-galactoside) and 6-methoxykaempferol-3-O-galactoside, astragalin, quercetin, kaempferol and isorhamnetin using two runs with different solvent system. Ethyl acetate-methanol-water (10:1:10, v/v) was selected by analytical HPCCC as the optimum phase system for the separation of patuletin-3-O-glucoside, a mixture of hyperoside and 6-methoxykaempferol-3-O-galactoside, and astragalin. A Dichloromethane-methanol-water (5:3:2, v/v) was used for the separation of quercetin, kaempferol and isorhamnetin. The separation was then scaled up: the crude extract (ca 1.5 g) was separated by preparative HPCCC, yielding 12 mg of patuletin-3-O-glucoside at a purity of 98.3%, yielding 9 mg of a mixture of hyperoside and 6-methoxykaempferol-3-O-galactoside constituting over 98% of the fraction, and 16 mg of astragalin (kaempferol-3-O-glucoside) at a purity of over 99%. The pump-out peaks are isorhanetin (98% purity), kaemferol (93% purity) and quercitin (99% purity). The chemical structure of patuletin-3-O-glucoside and astragalin were confirmed by MS and ¹H, ¹³C NMR. Copyright © 2011 Elsevier B.V. All rights reserved.

  11. Interactions of milk α- and β-casein with malvidin-3-O-glucoside and their effects on the stability of grape skin anthocyanin extracts.

    Science.gov (United States)

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

    2016-05-15

    The interactions of α- and β-casein with malvidin-3-O-glucoside (MG), the major anthocyanin in grape skin anthocyanin extracts (GSAE), were examined at pH 6.3 by fluorescence, fourier transform infrared (FTIR) and circular dichroism (CD) spectroscopy. The binding constant (KS), binding force and effects of the interactions on the caseins conformation and GSAE stability were investigated. The results showed that α- and β-casein bound with MG via hydrophilic (van der Waals forces or hydrogen bonding) and hydrophobic interactions, respectively. α-Casein had a slightly stronger binding affinity toward MG than β-casein, with respective KS values of 0.51×10(3)M(-1) and 0.46×10(3)M(-1) at 297K. The secondary structures of α- and β-casein were changed by MG binding, with a decrease in α-helix and an increase in turn for α-casein and no change in α-helix and a decrease in turn for β-casein. The casein-anthocyanin interaction appeared to have a positive effect on the thermal, oxidation and photo stability of GSAE. Copyright © 2015 Elsevier Ltd. All rights reserved.

  12. Cytotoxicity, Antioxidant and Apoptosis Studies of Quercetin-3-O Glucoside and 4-(β-D-Glucopyranosyl-1→4-α-L-Rhamnopyranosyloxy)-Benzyl Isothiocyanate from Moringa oleifera.

    Science.gov (United States)

    Maiyo, Fiona C; Moodley, Roshila; Singh, Moganavelli

    2016-01-01

    Moringa oleifera, from the family Moringaceae, is used as a source of vegetable and herbal medicine and in the treatment of various cancers in many African countries, including Kenya. The present study involved the phytochemical analyses of the crude extracts of M.oleifera and biological activities (antioxidant, cytotoxicity and induction of apoptosis in-vitro) of selected isolated compounds. The compounds isolated from the leaves and seeds of the plant were quercetin-3-O-glucoside (1), 4-(β-D-glucopyranosyl-1→4-α-L-rhamnopyranosyloxy)-benzyl isothiocyanate (2), lutein (3), and sitosterol (4). Antioxidant activity of compound 1 was significant when compared to that of the control, while compound 2 showed moderate activity. The cytotoxicity of compounds 1 and 2 were tested in three cell lines, viz. liver hepatocellular carcinoma (HepG2), colon carcinoma (Caco-2) and a non-cancer cell line Human Embryonic Kidney (HEK293), using the MTT cell viability assay and compared against a standard anticancer drug, 5-fluorouracil. Apoptosis studies were carried out using the acridine orange/ethidium bromide dual staining method. The isolated compounds showed selective in vitro cytotoxic and apoptotic activity against human cancer and non-cancer cell lines, respectively. Compound 1 showed significant cytotoxicity against the Caco-2 cell line with an IC50 of 79 μg mL(-1) and moderate cytotoxicity against the HepG2 cell line with an IC50 of 150 μg mL(-1), while compound 2 showed significant cytotoxicity against the Caco- 2 and HepG2 cell lines with an IC50 of 45 μg mL(-1) and 60 μg mL(-1), respectively. Comparatively both compounds showed much lower cytotoxicity against the HEK293 cell line with IC50 values of 186 μg mL(-1) and 224 μg mL(-1), respectively.

  13. Colorimetric study of malvidin-3-O-glucoside copigmented by phenolic compounds: The effect of molar ratio, temperature, pH, and ethanol content on color expression of red wine model solutions.

    Science.gov (United States)

    Zhang, Bo; Yang, Xue-Shan; Li, Ning-Ning; Zhu, Xia; Sheng, Wen-Jun; He, Fei; Duan, Chang-Qing; Han, Shun-Yu

    2017-12-01

    In the recent research, the copigmentations of malvidin-3-O-glucoside with eight types of phenolic copigments have been investigated. The influence of the pigment/copigment molar ratio, the reaction temperature, the pH and the ethanol content of solutions has been examined. The results showed that the copigmentation effect was dependent on not only the particular structures of the phenolic compounds but also the factors of the reaction systems. The increase of the copigment concentration can strengthen the copigmentation effect, improve the solution color, and enhance the red-purple features. Different temperatures had different influences on the copigmentation reactions. The destruction of the copigmentation complexes can result in the hypsochromic shift of the reaction solution when the temperature was higher than 20°C. The bathochromic shift of the solution gradually progressed with the increase of the pH value. A significant copigmentation feature was spotted when pH reached 3.0, which demonstrates obvious red-purple characterization. The addition of the ethanol weakened the copigmentation effect. According to measurement through color analysis, it was found that the color differences caused by ethanol in red wine were typically attributed to quantitative changes. Remarkably, all of the above delicate color deviations caused by the structural or environmental factors can be precisely and conveniently depicted via the CIELAB space analysis. Copyright © 2017 Elsevier Ltd. All rights reserved.

  14. Degradation kinetics of cyanidin 3-O-glucoside and cyanidin 3-O-rutinoside during hot air and vacuum drying in mulberry (Morus alba L.) fruit: A comparative study based on solid food system.

    Science.gov (United States)

    Zhou, Mo; Chen, Qinqin; Bi, Jinfeng; Wang, Yixiu; Wu, Xinye

    2017-08-15

    The aim of this study is to ascertain the degradation kinetic of anthocyanin in dehydration process of solid food system. Mulberry fruit was treated by hot air and vacuum drying at 60 and 75°C. The contents of cyanidin 3-O-glucoside and cyanidin 3-O-rutinoside were determined by using high performance liquid chromatography. Kinetic and thermodynamic parameters were calculated for analysing the degradation characteristics. Model fitting results showed monomeric anthocyanin degradations were followed the second-order kinetic. Vacuum drying presented high kinetic rate constants and low t 1/2 values. Thermodynamic parameters including the activation energy, enthalpy change and entropy change appeared significant differences between hot air and vacuum drying. Both heating techniques showed similar effects on polyphenol oxidase activities. These results indicate the anthocyanin degradation kinetic in solid food system is different from that in liquid and the oxygen can be regarded as a catalyst to accelerate the degradation. Copyright © 2017 Elsevier Ltd. All rights reserved.

  15. Proanthocyanidin synthesis in Theobroma cacao: genes encoding anthocyanidin synthase, anthocyanidin reductase, and leucoanthocyanidin reductase.

    Science.gov (United States)

    Liu, Yi; Shi, Zi; Maximova, Siela; Payne, Mark J; Guiltinan, Mark J

    2013-12-05

    The proanthocyanidins (PAs), a subgroup of flavonoids, accumulate to levels of approximately 10% total dry weight of cacao seeds. PAs have been associated with human health benefits and also play important roles in pest and disease defense throughout the plant. To dissect the genetic basis of PA biosynthetic pathway in cacao (Theobroma cacao), we have isolated three genes encoding key PA synthesis enzymes, anthocyanidin synthase (ANS), anthocyanidin reductase (ANR) and leucoanthocyanidin reductase (LAR). We measured the expression levels of TcANR, TcANS and TcLAR and PA content in cacao leaves, flowers, pod exocarp and seeds. In all tissues examined, all three genes were abundantly expressed and well correlated with PA accumulation levels, suggesting their active roles in PA synthesis. Overexpression of TcANR in an Arabidopsis ban mutant complemented the PA deficient phenotype in seeds and resulted in reduced anthocyanidin levels in hypocotyls. Overexpression of TcANS in tobacco resulted in increased content of both anthocyanidins and PAs in flower petals. Overexpression of TcANS in an Arabidopsis ldox mutant complemented its PA deficient phenotype in seeds. Recombinant TcLAR protein converted leucoanthocyanidin to catechin in vitro. Transgenic tobacco overexpressing TcLAR had decreased amounts of anthocyanidins and increased PAs. Overexpressing TcLAR in Arabidopsis ldox mutant also resulted in elevated synthesis of not only catechin but also epicatechin. Our results confirm the in vivo function of cacao ANS and ANR predicted based on sequence homology to previously characterized enzymes from other species. In addition, our results provide a clear functional analysis of a LAR gene in vivo.

  16. Molecular Mechanisms Behind the Chemopreventive Effects of Anthocyanidins

    Directory of Open Access Journals (Sweden)

    De-Xing Hou

    2004-01-01

    Full Text Available Anthocyanins are polyphenolic ring-based flavonoids, and are widespread in fruits and vegetables of red-blue color. Epidemiological investigations and animal experiments have indicated that anthocyanins may contribute to cancer chemoprevention. The studies on the mechanism have been done recently at molecular level. This review summarizes current molecular bases for anthocyanidins on several key steps involved in cancer chemoprevention: (i inhibition of anthocyanidins in cell transformation through targeting mitogen-activated protein kinase (MAPK pathway and activator protein 1 (AP-1 factor; (ii suppression of anthocyanidins in inflammation and carcinogenesis through targeting nuclear factor kappa B (NF-κB pathway and cyclooxygenase 2 (COX-2 gene; (iii apoptotic induction of cancer cells by anthocyanidins through reactive oxygen species (ROS / c-Jun NH2-terminal kinase (JNK-mediated caspase activation. These data provide a first molecular view of anthocyanidins contributing to cancer chemoprevention.

  17. Anthocyanins standards (cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside isolation from freeze-dried açaí (Euterpe oleraceae Mart. by HPLC Isolamento de padrões de antocianinas (cianidina-3-O-glucosídeo e cianidina -3-O-rutinosídeo de açaí liofilizado (Euterpe oleraceae Mart. por CLAE

    Directory of Open Access Journals (Sweden)

    Ana Cristina Miranda Senna Gouvêa

    2012-03-01

    Full Text Available Availability of analytical standards is a critical aspect in developing methods for quantitative analysis of anthocyanins. The anthocyanins cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside were isolated from samples of freeze-dried açaí (Euterpe oleraceae Mart., which is a round and purple well-known palm fruit in Brazil, and then used as standards. The isolation of the anthocyanins was performed by High Performance Liquid Chromatography (HPLC, using an adapted six-channel selection valve. The identification of anthocyanin pigments in açaí was based on mass spectrometric data for molecular ions and MS-MS product ions and on previous published data. After the collection procedure, standards with a high purity grade were obtained and an external standard curve of each anthocyanin was plotted.Disponibilidade de padrões analíticos é um aspecto crítico no desenvolvimento de métodos de análises quantitativas de antocianinas. Para a obtenção dos padrões isolados de antocianinas cianidina-3-O-glicosídeo e cianidina-3-O-rutinosídeo foram utilizadas amostras liofilizadas de açaí (Euterpe oleraceae Mart., que é um conhecido fruto de palmeiras no Brasil de forma arredondada e roxo. O isolamento das antocianinas foi realizado por Cromatografia Líquida de Alta Eficiência (CLAE, utilizando uma válvula seletora de seis canais. A identificação de antocianinas no açaí foi baseada em dados publicados na literatura e por espectrometria de massas. Após a coleta, padrões com um alto grau de pureza foram obtidos e uma curva para padronização externa de cada antocianina foi feita.

  18. Changes in anthocyanidin levels during the maturation of color-fleshed potato (Solanum tuberosum L.) tubers.

    Science.gov (United States)

    Šulc, Miloslav; Kotíková, Zora; Paznocht, Luboš; Pivec, Vladimír; Hamouz, Karel; Lachman, Jaromír

    2017-12-15

    Certain potato cultivars are capable of producing anthocyanin pigments in the potato skin and flesh and those pigments have been shown, together with other phytochemicals, to promote good health. Six common anthocyanidins (cyanidin, delphinidin, petunidin, pelargonidin, malvidin and peonidin) were analyzed weekly for 15weeks in red- and purple-fleshed potato cultivars (Red Emma, Königspurpur, Valfi and Blaue de la Mancha) grown in field conditions using a validated LC-(+ESI)MS/MS method. Pelargonidin was the major type detected in red-fleshed cultivars whereas petunidin was the major type detected in the purple ones. Neither cyanidin nor delphinidin were found in any of the cultivars. The anthocyanidin levels observed were as high as 78mg/100g FW during tuber growth; however, fully matured tubers contained only 10-39mg anthocyanidins/100gFW. Anthocyanidin levels were moderately correlated with global solar irradiation (r<0.6252) but not with rainfall or daily temperature. Copyright © 2017 Elsevier Ltd. All rights reserved.

  19. Medicinal significance, pharmacological activities, and analytical aspects of anthocyanidins ‘delphinidin’: A concise report

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    Kanika Patel

    2013-01-01

    Full Text Available Herbal medicines have been used for the treatment of various disorders in the world since a very early age due to easily available and less side effect. A large number of phytochemicals have been derived directly or indirectly from natural sources in the form of oils, food supplement, neutraceuticals, and colour pigments. Anthocyanins are classes of phytoconstituents mainly responsible for the different colors of plants material. Literature report revealed the presence of different anthocyanidins such as cyanidin, delphinidin, petunidin, peonidin, pelargonidin, malvidin, cyaniding etc. These anthocyanidins showed a wide range of pharmacological activities. Anthocyanins have an attractive profile in the food industry as natural colorants due to its possible health benefits and safety issues compared to the synthetic dye. Delphinidin is an important anthocyanidins mainly present in the epidermal tissues of flowers and fruits. Delphinidin showed various pharmacological activities such as antioxidant, antimutagenesis, anti-inflammatory and antiangiogenic etc. This review was aimed to elaborate the medicinal importance, pharmacological activities and analytical aspects of anthocyanidins ‘delphinidin’. This review will be benificial to the scientist, manufacturer and consumers in order to explore the potential health benefits of delphinidin.

  20. Anthocyanidins and anthocyanins: colored pigments as food, pharmaceutical ingredients, and the potential health benefits.

    Science.gov (United States)

    Khoo, Hock Eng; Azlan, Azrina; Tang, Sou Teng; Lim, See Meng

    2017-01-01

    Anthocyanins are colored water-soluble pigments belonging to the phenolic group. The pigments are in glycosylated forms. Anthocyanins responsible for the colors, red, purple, and blue, are in fruits and vegetables. Berries, currants, grapes, and some tropical fruits have high anthocyanins content. Red to purplish blue-colored leafy vegetables, grains, roots, and tubers are the edible vegetables that contain a high level of anthocyanins. Among the anthocyanin pigments, cyanidin-3-glucoside is the major anthocyanin found in most of the plants. The colored anthocyanin pigments have been traditionally used as a natural food colorant. The color and stability of these pigments are influenced by pH, light, temperature, and structure. In acidic condition, anthocyanins appear as red but turn blue when the pH increases. Chromatography has been largely applied in extraction, separation, and quantification of anthocyanins. Besides the use of anthocyanidins and anthocyanins as natural dyes, these colored pigments are potential pharmaceutical ingredients that give various beneficial health effects. Scientific studies, such as cell culture studies, animal models, and human clinical trials, show that anthocyanidins and anthocyanins possess antioxidative and antimicrobial activities, improve visual and neurological health, and protect against various non-communicable diseases. These studies confer the health effects of anthocyanidins and anthocyanins, which are due to their potent antioxidant properties. Different mechanisms and pathways are involved in the protective effects, including free-radical scavenging pathway, cyclooxygenase pathway, mitogen-activated protein kinase pathway, and inflammatory cytokines signaling. Therefore, this review focuses on the role of anthocyanidins and anthocyanins as natural food colorants and their nutraceutical properties for health. Abbreviations : CVD: Cardiovascular disease VEGF: Vascular endothelial growth factor.

  1. Cooked blueberries: anthocyanin and anthocyanidin degradation and their radical-scavenging activity.

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    Oliveira, Carla; Amaro, L Filipe; Pinho, Olivia; Ferreira, Isabel M P L V O

    2010-08-25

    This study examined anthocyanin and anthocyanidin composition and radical-scavenging activity of three cultivars of blueberries (Vaccinium corymbosum L., cv. Bluecrop, Bluetravel, and Ozarkblue) before and after cooking. A total of 13 anthocyanins were separated and monitored in methanolic extracts of raw fruits by high-performance liquid chromatography/diode array detector (HPLC/DAD). Principal component analysis using the anthocyanin profile as variables revealed differences according to cultivar origin. Of the six common anthocyanidins, four were identified and quantified in the hydrolysates, namely, malvidin, the most abundant, followed by cyanidin, petunidin, and delphynidin. A systematic evaluation of the degradation of anthocyanins and anthocyanidins of blueberries cooked in stuffed fish was performed. The percentage of anthocyanin degradation in cooked blueberries (by progressive heating from 12 to 99 °C for 60 min) ranged between 16 and 30% for Bluecrop, 30-42% for Bluetravel, and 12-41% for Ozarkblue. However, cooked blueberries maintained or increased radical-scavenging activity when evaluated by the 1,1'-diphenyl-2-picrylhydrazyl (DPPH) method. Overall, results show that cooked blueberries can serve as a good source of bioactive phytochemicals.

  2. ISOLATION OF ANTHOCYANIDIN FROM WORA-WARI FLOWERS (Hibiscus rosa sinensis L. AND ITS APPLICATION AS INDICATORS OF ACID-BASE

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    Siti Nuryanti

    2013-11-01

    Full Text Available Wora-wari plants are easily cultivated and founded in Indonesia, also their bloomy is not seasonal. Isolation of anthocyanidin from Wora-wari was done by maceration using n-hexane, ethyl acetate and methanol-HCl 1.0% and isolation of anthocyanidin was performed by column chromatography. Identification for structure of anthocyanidin was done by UV-Vis spectrophotometer, FT-IR, 1H- and 13C-NMR along with color reagent. In the Wora-wari flowers, it has been identified the existence of anthocyanidin pelargonidin. The color change of anthocyanidin pelargonidin results in acid solution was red and base solution was green. Keywords: Wora-wari flower, anthocyanidin, acid-base indicator

  3. Effects of spray drying on antioxidant capacity and anthocyanidin content of blueberry by-products.

    Science.gov (United States)

    Lim, Kar; Ma, Mitzi; Dolan, Kirk D

    2011-09-01

    The effect of spray drying on degradation of nutraceutical components in cull blueberry extract was investigated. Samples collected before and after spray drying were tested for antioxidant capacity using oxygen radical absorbance capacity (ORAC(FL) ) and total phenolics; and for individual anthocyanidins. In Study 1, four different levels of maltodextrin (blueberry solids to maltodextrin ratios of 5: 95, 10: 90, 30: 70, and 50: 50) were spray dried a pilot-scale spray dryer. There was significantly higher retention of nutraceutical components with increased levels of maltodextrin indicating a protective effect of maltodextrin on the nutraceutical components during spray drying. In Study 2, the air inlet temperature of the spray dryer was kept constant for all runs at 150 °C, with 2 different outlet temperatures of 80 and 90 °C. The degradation of nutraceutical components was not significantly different at the 2 selected outlet temperatures. ORAC(FL) reduction for blueberry samples after spray drying was 66.3% to 69.6%. After spray drying, total phenolics reduction for blueberry was 8.2% to 17.5%. Individual anthocyanidin reduction for blueberry was 50% to 70%. The experimental spray dried powders compared favorably to commercial blueberry powders. Results of the study show that use of blueberry by-products is feasible to make a value-added powder. Results can be used by producers to estimate final nutraceutical content of spray-dried blueberry by-products. © 2011 Institute of Food Technologists®

  4. Energetic and electronic computation of the two-hydrogen atom donation process in catecholic and non-catecholic anthocyanidins.

    Science.gov (United States)

    Ali, Hussein M; Ali, Isra H

    2018-03-15

    Antioxidant activity of anthocyanidins is greatly affected by the 3-hydroxyl group and/or a catecholic moiety. The two-hydrogen atom donation process is frequently used to explain the high antioxidant activity of polyphenolic compounds leading to the formation of stable diketones e.g. 1,2-quinones. Thermodynamic parameters, HOMO and spin density were computed to identify the favoured path, either through the 3-hydroxyl group or through the catecholic moiety in a series of catecholic and non-catecholic 3-oxy- (and deoxy)-anthocyanidins. DFT calculations showed that the donation process in non-catecholic anthocyanidins depended on the substituents on ring B. Anthocyanidins with 3',5'-diOMe groups showed donation through 3,4'-OH or, otherwise, through 3,5-OH groups. Catecholic 3-oxyanthocyanidins, on the other hand, showed donation through the 3,4'-OH path rather than the catecholic path (4',3'-path). The 3,4'-path was favoured by the formation of planar 3-radicals in the first step and the stabilization of 4'-radicals in the second step by H-bonding with the 3'-OH group. Copyright © 2017 Elsevier Ltd. All rights reserved.

  5. Volatile, anthocyanidin, quality and sensory changes in rabbiteye blueberry from whole fruit through pilot plant juice processing.

    Science.gov (United States)

    Beaulieu, John C; Stein-Chisholm, Rebecca E; Lloyd, Steven W; Bett-Garber, Karen L; Grimm, Casey C; Watson, Michael A; Lea, Jeanne M

    2017-01-01

    High antioxidant content and keen marketing have increased blueberry demand and increased local production which in turn mandates new uses for abundant harvests. Pilot scale processes were employed to investigate the anthocyanidin profiles, qualitative volatile compositions, and sensorial attributes in not-from-concentrate (NFC) 'Tifblue' rabbiteye blueberry juices. Processing prior to pasteurization generally resulted in increased L * and hue angle color, while a * , b * , and C * decreased. After 4 months pasteurized storage, non-clarified juice (NCP) lost 73.8% of total volatiles compared with 70.9% in clarified juice (CJP). There was a total anthocyanidin decrease of 84.5% and 85.5% after 4 months storage in NCP and CJP, respectively. Storage itself resulted in only 14.2% and 7.2% anthocyanidin loss after pasteurization in NCP and CJP. Storage significantly affected nine flavor properties in juices; however, there were no significant differences in the blueberry, strawberry, purple grape, floral, sweet aroma, or sweet tastes between processed and stored juices. NFC pasteurized blueberry juices maintained desirable flavors even though highly significant volatile and anthocyanidin losses occurred through processing. Maintenance of color and flavor indicate that NFC juices could have an advantage over more abusive methods often used in commercial juice operations. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

  6. Ground and excited state properties of high performance anthocyanidin dyes-sensitized solar cells in the basic solutions

    Energy Technology Data Exchange (ETDEWEB)

    Prima, Eka Cahya [Advanced Functional Material Laboratory, Engineering Physics, Institut Teknologi Bandung (Indonesia); Computational Material Design and Quantum Engineering Laboratory, Engineering Physics, Institut Teknologi Bandung (Indonesia); International Program on Science Education, Universitas Pendidikan Indonesia (Indonesia); Yuliarto, Brian; Suyatman, E-mail: yatman@tf.itb.ac.id [Advanced Functional Material Laboratory, Engineering Physics, Institut Teknologi Bandung (Indonesia); Dipojono, Hermawan Kresno [Computational Material Design and Quantum Engineering Laboratory, Engineering Physics, Institut Teknologi Bandung (Indonesia)

    2015-09-30

    The aglycones of anthocyanidin dyes were previously reported to form carbinol pseudobase, cis-chalcone, and trans-chalcone due to the basic levels. The further investigations of ground and excited state properties of the dyes were characterized using density functional theory with PCM(UFF)/B3LYP/6-31+G(d,p) level in the basic solutions. However, to the best of our knowledge, the theoretical investigation of their potential photosensitizers has never been reported before. In this paper, the theoretical photovoltaic properties sensitized by dyes have been successfully investigated including the electron injections, the ground and excited state oxidation potentials, the estimated open circuit voltages, and the light harvesting efficiencies. The results prove that the electronic properties represented by dyes’ LUMO-HOMO levels will affect to the photovoltaic performances. Cis-chalcone dye is the best anthocyanidin aglycone dye with the electron injection spontaneity of −1.208 eV, the theoretical open circuit voltage of 1.781 V, and light harvesting efficiency of 56.55% due to the best HOMO-LUMO levels. Moreover, the ethanol solvent slightly contributes to the better cell performance than the water solvent dye because of the better oxidation potential stabilization in the ground state as well as in the excited state. These results are in good agreement with the known experimental report that the aglycones of anthocyanidin dyes in basic solvent are the high potential photosensitizers for dye-sensitized solar cell.

  7. Molecular cloning and functional characterization of the anthocyanidin reductase gene from Vitis bellula.

    Science.gov (United States)

    Zhu, Yue; Peng, Qing-Zhong; Li, Ke-Gang; Xie, De-Yu

    2014-08-01

    Anthocyanidin reductase (ANR) is an NADPH-/NADH-dependent enzyme that transfers two hydrides to anthocyanidins to produce three types of isomeric flavan-3-ols. This reductase forms the ANR pathway toward the biosynthesis of proanthocyanidins (PAs, which are also called condensed tannins). Here, we report cloning and functional characterization of an ANR (called VbANR) homolog from the leaves of Vitis bellula, a newly developed grape crop in southern China. The open reading frame (ORF) of VbANR is 1,017 bp in length and encodes 339 amino acids. A phylogenetic analysis and an alignment using 17 sequences revealed that VbANR is approximately 99.9 % identical to the ANR homolog from Vitis vinifera. The VbANR ORF is fused to the Trx gene containing a His-tag in the pET32a(+) vector to obtain a pET32a(+)-VbANR construct for expressing the recombinant VbANR. In vitro enzyme assays show that VbANR converts cyanidin, delphinidin, and pelargonidin to their corresponding flavan-3-ols. Enzymatic products include 2S,3R-trans- and 2R,3R-cis-flavan-3-ols isomers, such as (-)-catechin and (-)-epicatechin. In addition, the third compound that is observed from the enzymatic products is most likely a 2S,3S-cis-flavan-3-ol. To analyze the kinetics and optimize pH and temperature values, a UV spectrometry method was developed to quantify the concentrations of total enzymatic products. The optimum pH and temperature values are 4.0 and 40 °C, respectively. The K m , K cat, V max, and K cat/K m values for pelargonidin and delphinidin were similar. In comparison, VbANR exhibits a slightly lower affinity to cyanidin. VbANR uses both NADPH and NADH but prefers to employ NADPH. GFP fusion and confocal microscopy analyses revealed the cytosolic localization of VbANR. The overexpression of VbANR in ban mutants reconstructed the biosynthetic pathway of PAs in the seed coat. These data demonstrate that VbANR forms the ANR pathway, leading to the formation of three types of isomeric flavan-3-ols

  8. Isolation and characterization of cDNAs encoding leucoanthocyanidin reductase and anthocyanidin reductase from Populus trichocarpa.

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    Lijun Wang

    Full Text Available Proanthocyanidins (PAs contribute to poplar defense mechanisms against biotic and abiotic stresses. Transcripts of PA biosynthetic genes accumulated rapidly in response to infection by the fungus Marssonina brunnea f.sp. multigermtubi, treatments of salicylic acid (SA and wounding, resulting in PA accumulation in poplar leaves. Anthocyanidin reductase (ANR and leucoanthocyanidin reductase (LAR are two key enzymes of the PA biosynthesis that produce the main subunits: (+-catechin and (--epicatechin required for formation of PA polymers. In Populus, ANR and LAR are encoded by at least two and three highly related genes, respectively. In this study, we isolated and functionally characterized genes PtrANR1 and PtrLAR1 from P. trichocarpa. Phylogenetic analysis shows that Populus ANR1 and LAR1 occurr in two distinct phylogenetic lineages, but both genes have little difference in their tissue distribution, preferentially expressed in roots. Overexpression of PtrANR1 in poplar resulted in a significant increase in PA levels but no impact on catechin levels. Antisense down-regulation of PtrANR1 showed reduced PA accumulation in transgenic lines, but increased levels of anthocyanin content. Ectopic expression of PtrLAR1 in poplar positively regulated the biosynthesis of PAs, whereas the accumulation of anthocyanin and flavonol was significantly reduced (P<0.05 in all transgenic plants compared to the control plants. These results suggest that both PtrANR1 and PtrLAR1 contribute to PA biosynthesis in Populus.

  9. Transcripts of Anthocyanidin Reductase and Leucoanthocyanidin Reductase and Measurement of Catechin and Epicatechin in Tartary Buckwheat

    Directory of Open Access Journals (Sweden)

    Yeon Bok Kim

    2014-01-01

    Full Text Available Anthocyanidin reductase (ANR and leucoanthocyanidin reductase (LAR play an important role in the monomeric units biosynthesis of proanthocyanidins (PAs such as catechin and epicatechin in several plants. The aim of this study was to clone ANR and LAR genes involved in PAs biosynthesis and examine the expression of these two genes in different organs under different growth conditions in two tartary buckwheat cultivars, Hokkai T8 and T10. Gene expression was carried out by quantitative real-time RT-PCR, and catechin and epicatechin content was analyzed by high performance liquid chromatography. The expression pattern of ANR and LAR did not match the accumulation pattern of PAs in different organs of two cultivars. Epicatechin content was the highest in the flowers of both cultivars and it was affected by light in only Hokkai T8 sprouts. ANR and LAR levels in tartary buckwheat might be regulated by different mechanisms for catechin and epicatechin biosynthesis under light and dark conditions.

  10. Direct and indirect inactivation of tumor cell protective catalase by salicylic acid and anthocyanidins reactivates intercellular ROS signaling and allows for synergistic effects.

    Science.gov (United States)

    Scheit, Katrin; Bauer, Georg

    2015-03-01

    Salicylic acid and anthocyanidins are known as plant-derived antioxidants, but also can provoke paradoxically seeming prooxidant effects in vitro. These prooxidant effects are connected to the potential of salicylic acid and anthocyanidins to induce apoptosis selectively in tumor cells in vitro and to inhibit tumor growth in animal models. Several epidemiological studies have shown that salicylic acid and its prodrug acetylsalicylic acid are tumor-preventive for humans. The mechanism of salicylic acid- and anthocyanidin-dependent antitumor effects has remained enigmatic so far. Extracellular apoptosis-inducing reactive oxygen species signaling through the NO/peroxynitrite and the HOCl signaling pathway specifically induces apoptosis in transformed cells. Tumor cells have acquired resistance against intercellular reactive oxygen species signaling through expression of membrane-associated catalase. Here, we show that salicylic acid and anthocyanidins inactivate tumor cell protective catalase and thus reactive apoptosis-inducing intercellular reactive oxygen species signaling of tumor cells and the mitochondrial pathway of apoptosis Salicylic acid inhibits catalase directly through its potential to transform compound I of catalase into the inactive compound II. In contrast, anthocyanidins provoke a complex mechanism for catalase inactivation that is initiated by anthocyanidin-mediated inhibition of NO dioxygenase. This allows the formation of extracellular singlet oxygen through the reaction between H(2)O(2) and peroxynitrite, amplification through a caspase8-dependent step and subsequent singlet oxygen-mediated inactivation of catalase. The combination of salicylic acid and anthocyanidins allows for a remarkable synergistic effect in apoptosis induction. This effect may be potentially useful to elaborate novel therapeutic approaches and crucial for the interpretation of epidemiological results related to the antitumor effects of secondary plant compounds. © The

  11. Mass spectrometric and enzymatic evidence confirm the existence of anthocyanidin 3,5-O-diglucosides in cabernet sauvignon (Vitis vinifera L.) grape berries.

    Science.gov (United States)

    Xing, Ran-Ran; Li, Si-Yu; He, Fei; Yang, Zhe; Duan, Chang-Qing; Li, Zheng; Wang, Jun; Pan, Qiu-Hong

    2015-04-01

    It has been widely accepted that anthocyanidin 3,5-O-diglucosides do not exist in Vitis vinifera L. Cabernet Sauvignon (CS) berries. However, our anthocyanin analyses using HPLC-ESI-MS/MS detected the existence of a low level of anthocyanidin 3,5-O-diglucosides in the Cabernet Sauvignon grape berries grown in China. The authenticity of these samples was confirmed with microsatellite markers. The existence of anthocyanidin 3,5-O-diglucoside was further verified by the enzymatic evidence for the first time. Four putative 5-O-glucosyltransferase (5GT) genes were isolated from the Cabernet Sauvignon berries. The enzymatic analysis showed that a recombinant protein (designated as Vv5GT3) glucosylated the 3-O- and 5-O-positions of anthocyanidins and flavonols. A phylogenetic analysis revealed that this bifunctional enzyme belongs to the 5GT subfamily of UDP-glycosyltransferases. This finding brought a new understanding of the anthocyanins' profile and their biosynthesis in V. vinifera and would be helpful for further investigations of the mechanism of accumulation of anthocyanidin diglucosides in Cabernet Sauvignon berries in China's wine-producing regions.

  12. Pharmacokinetics of anthocyanidin-3-glycosides following consumption of Hibiscus sabdariffa L. extract.

    Science.gov (United States)

    Frank, Thomas; Janssen, Marlies; Netzel, Michael; Strass, Gabriele; Kler, Adolf; Kriesl, Erwin; Bitsch, Irmgard

    2005-02-01

    Pharmacokinetic parameters of several dietary anthocyanins following consumption of Hibiscus sabdariffa L. extract were determined in 6 healthy volunteers. Subjects were given a single oral dose of 150 mL of Hibiscus sabdariffa L. extract yielding 62.6 mg of cyanidin-3-sambubioside, 81.6 mg of delphindin-3-sambubioside, and 147.4 mg of total anthocyanins (calculated as cyanidin equivalents). Within 7 hours, the urinary excretion of cyanidin-3-sambubioside, delphinidin-3-sambubioside, and total anthocyanins (ie, the sum of all quantifiable anthocyanidin glycosides) was 0.016%, 0.021%, and 0.018% of the administered doses, respectively. Maximum excretion rates were determined at 1.5 to 2.0 hours after intake. The dose-normalized plasma area under the curve estimates were 0.076, 0.032, and 0.050 ng x h/mL/mg for cyanidin-3-sambubioside, delphinidin-3-sambubioside, and total anthocyanins, respectively. The dose-normalized C(max) estimates were 0.036, 0.015, and 0.023 ng/mL/mg in the same sequence. They were reached each at 1.5 hours (median) after intake. The geometric means of t1/2 were 2.18, 3.34, and 2.63 hours for cyanidin-3-sambubioside, delphinidin-3-sambubioside, and total anthocyanins, respectively. The urinary excretion of intact anthocyanins was fast and appeared to be monoexponential. To evaluate the contribution of anthocyanins to the health-protecting effects of Hibiscus sabdariffa L. extract, it will be necessary to perform further studies on both the intact glycosides and their in vivo metabolites or conjugates in human plasma and urine.

  13. Genetic analysis and QTL mapping for fruit skin anthocyanidin in grape (vitis vinifera)

    International Nuclear Information System (INIS)

    Guo, Y.; Xue, R.; Lin, H.; Su, K.; Zhao, Y.; Zhendong, L.; Shi, G.; Niu, Z.; Li, K.; Guo, X.

    2015-01-01

    In this study, an F1 population was created by the cross 87-1*9-22. The female parent 87-1 was a black purple cultivar and the male parent was an excellent breeding line with green pericarp. the skin color separation of population and distribution, and determined the content of each individual fruit peel pigment. On the basis of the genetic map of Vitis vinifera L. We carried out the grape skin pigment content quantitative trait locus (QTL) analyses. The results show that the fruit color performance for continuous variation and the inheritance of fruit skin anthocyanidin content was a quantitative inheritance. The color of offspring ranges from green and black-blue and existing distribution. Using SSR and SRAP molecular markers to construct 188 female parent maps,175 male parent maps and 251 consensus maps, and the total map distance is 1047.5 cM,1100.2 cM and 1264.2 cM respectively. The result of QTL showed that there were more QTLs exist in the linkage group of 1, 2, 3, 4, 9, 13, 14, 16 and 19 and in the linkage group of 3, 4, 13 and 14, we detected QTLs in the similar position with the result of the study in the year of 2011 and 2012, and based on this we will conduct the fine QTL location in the future, this result will lay a good foundation for the grape in the department of molecular assistant breeding in the future. (author)

  14. LC–MS/MS and UPLC–UV Evaluation of Anthocyanins and Anthocyanidins during Rabbiteye Blueberry Juice Processing

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    Rebecca E. Stein-Chisholm

    2017-11-01

    Full Text Available Blueberry juice processing includes multiple steps and each one affects the chemical composition of the berries, including thermal degradation of anthocyanins. Not-from-concentrate juice was made by heating and enzyme processing blueberries before pressing, followed by ultrafiltration and pasteurization. Using LC–MS/MS, major and minor anthocyanins were identified and semi-quantified at various steps through the process. Ten anthocyanins were identified, including 5 arabinoside and 5 pyrannoside anthocyanins. Three minor anthocyanins were also identified, which apparently have not been previously reported in rabbiteye blueberries. These were delphinidin-3-(p-coumaroyl-glucoside, cyanidin-3-(p-coumaroyl-glucoside, and petunidin-3-(p-coumaroyl-glucoside. Delphinidin-3-(p-coumaroyl-glucoside significantly increased 50% after pressing. The five known anthocyanidins—cyanidin, delphinidin, malvidin, peonidin, and petunidin—were also quantitated using UPLC–UV. Raw berries and press cake contained the highest anthocyanidin contents and contribute to the value and interest of press cake for use in other food and non-food products. Losses of 75.7% after pressing and 12% after pasteurization were determined for anthocyanidins during not-from-concentrate juice processing.

  15. Overexpression of the Anthocyanidin Synthase Gene in Strawberry Enhances Antioxidant Capacity and Cytotoxic Effects on Human Hepatic Cancer Cells.

    Science.gov (United States)

    Giampieri, Francesca; Gasparrini, Massimiliano; Forbes-Hernandez, Tamara Y; Mazzoni, Luca; Capocasa, Franco; Sabbadini, Silvia; Alvarez-Suarez, Josè M; Afrin, Sadia; Rosati, Carlo; Pandolfini, Tiziana; Molesini, Barbara; Sánchez-Sevilla, José F; Amaya, Iraida; Mezzetti, Bruno; Battino, Maurizio

    2018-01-24

    Food fortification through the increase and/or modulation of bioactive compounds has become a major goal for preventing several diseases, including cancer. Here, strawberry lines of cv. Calypso transformed with a construct containing an anthocyanidin synthase (ANS) gene were produced to study the effects on anthocyanin biosynthesis, metabolism, and transcriptome. Three strawberry ANS transgenic lines (ANS L5, ANS L15, and ANS L18) were analyzed for phytochemical composition and total antioxidant capacity (TAC), and their fruit extracts were assessed for cytotoxic effects on hepatocellular carcinoma. ANS L18 fruits had the highest levels of total phenolics and flavonoids, while those of ANS L15 had the highest anthocyanin concentration; TAC positively correlated with total polyphenol content. Fruit transcriptome was also specifically affected in the polyphenol biosynthesis and in other related metabolic pathways. Fruit extracts of all lines exerted cytotoxic effects in a dose/time-dependent manner, increasing cellular apoptosis and free radical levels and impairing mitochondrial functionality.

  16. Flavor of fresh blueberry juice and the comparison to amount of sugars, acids, anthocyanidins, and physicochemical measurements.

    Science.gov (United States)

    Bett-Garber, Karen L; Lea, Jeanne M; Watson, Michael A; Grimm, Casey C; Lloyd, Steven W; Beaulieu, John C; Stein-Chisholm, Rebecca E; Andrzejewski, Brett P; Marshall, Donna A

    2015-04-01

    Six cultivars of southern highbush (SHB) and rabbiteye (RE) blueberry samples were harvested on 2 different dates. Each treatment combination was pressed 2 times for repeated measures. Fresh juice was characterized for 18 flavor/taste/feeling factor attributes by a descriptive flavor panel. Each sample was measured for sugars, acids, anthocyanidins, Folin-Ciocalteu, soluble solids (BRIX), titratable acidity (TA), and antioxidant capacity (ORACFL ). Flavors were correlated with the composition and physicochemical data. Blueberry flavor correlated with 3 parameters, and negatively correlated with 2. Strawberry correlated with oxalic acid and negatively correlated with sucrose and quinic acid. Sweet aroma correlated with oxalic and citric acid, but negatively correlated with sucrose, quinic, and total acids. Sweet taste correlated with 11 parameters, including the anthocyanidins; and negatively correlated with 3 parameters. Neither bitter nor astringent correlated with any of the antioxidant parameters, but both correlated with total acids. Sour correlated with total acids and TA, while negatively correlating with pH and BRIX:TA. Throat burn correlated with total acids and TA. Principal component analysis negatively related blueberry, sweet aroma, and sweet to sour, bitter, astringent, tongue tingle, and tongue numbness. The information in this component was related to pH, TA, and BRIX:TA ratio. Another principal component related the nonblueberry fruit flavors to BRIX. This PC, also divided the SHB berries from the RE. This work shows that the impact of juice composition on flavor is very complicated and that estimating flavor with physicochemical parameters is complicated by the composition of the juice. © 2015 Institute of Food Technologists®

  17. Cyanidin-3-O-Glucoside Modulates the In Vitro Inflammatory Crosstalk between Intestinal Epithelial and Endothelial Cells

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    Daniela Ferrari

    2017-01-01

    Full Text Available Intestinal epithelium represents a protective physical barrier and actively contributes to the mucosal immune system. Polarized basolateral intestinal secretion of inflammatory mediators, followed by activation of NF-κB signaling and inflammatory pathways in endothelial cells, efficiently triggers extravasation of neutrophils from the vasculature, therefore contributing to the development and maintenance of intestinal inflammation. Proper regulation of NF-κB activation at the epithelial interface is crucial for the maintenance of physiological tissue homeostasis. Many papers reported that anthocyanins, a group of compounds belonging to flavonoids, possess anti-inflammatory effects and modulate NF-κB activity. In this study, by using a coculture in vitro system, we aimed to evaluate the effects of TNF-α-stimulated intestinal cells on endothelial cells activation, as well as the protective effects of cyanidin-3-glucoside (C3G. In this model, TNF-α induced nuclear translocation of NF-κB and TNF-α and IL-8 gene expression in Caco-2 cells, whereas C3G pretreatment dose-dependently reduced these effects. Furthermore, TNF-α-stimulated Caco-2 cells induced endothelial cells activation with increased E-selectin and VCAM-1 mRNA, leukocyte adhesion, and NF-κB levels in HUVECs, which were inhibited by C3G. We demonstrated that selective inhibition of the NF-κB pathway in epithelial cells represents the main mechanism by which C3G exerts these protective effects. Thus, anthocyanins could contribute to the management of chronic gut inflammatory diseases.

  18. The L locus, one of complementary genes required for anthocyanin production in onions (Allium cepa), encodes anthocyanidin synthase.

    Science.gov (United States)

    Kim, Sunggil; Jones, Rick; Yoo, Kil-Sun; Pike, Leonard M

    2005-06-01

    Bulb color in onions (Allium cepa) is an important trait, but its complex, unclear mechanism of inheritance has been a limiting factor in onion cultivar improvement. The identity of the L locus, which is involved in the color difference between Brazilian yellow and red onions, is revealed in this study. A cross was made between a US-type yellow breeding line and a Brazilian yellow cultivar. The segregation ratio of nine red to seven yellow onions in the F(2) population supports the involvement of two complementary genes in anthocyanin production in the F(1) hybrids. The high-performance liquid chromatography (HPLC) and reverse-transcriptase (RT)-PCR analysis of the Brazilian yellow onions indicated that the genes are involved late in the anthocyanin synthesis pathway. The genomic sequence of the anthocyanidin synthase (ANS) gene in Brazilian yellow onions showed a point mutation, which results in an amino acid change of a glycine to an arginine at residue 229. Because this residue is located adjacent to a highly conserved iron-binding active site, this mutation is likely responsible for the inactivation of the ANS gene in Brazilian yellow onions. Following the isolation of the promoter sequence of the mutant allele, a PCR-based marker for allelic selection of the ANS gene was designed. This assay is based on an insertion (larger than 3 kb) mutation. The marker perfectly co-segregated with the color phenotypes in the F(2) populations, thereby indicating that the L locus encodes ANS.

  19. The anthocyanidin delphinidin mobilizes endogenous copper ions from human lymphocytes leading to oxidative degradation of cellular DNA

    International Nuclear Information System (INIS)

    Hanif, Sarmad; Shamim, Uzma; Ullah, M.F.; Azmi, Asfar S.; Bhat, Showket H.; Hadi, S.M.

    2008-01-01

    Epidemiological and experimental evidence exists to suggest that pomegranate and its juice possess chemopreventive and anticancer properties. The anthocyanidin delphinidin is a major polyphenol present in pomegranates and has been shown to be responsible for these effects. Plant polyphenols are recognized as naturally occurring antioxidants but also catalyze oxidative DNA degradation of cellular DNA either alone or in the presence of transition metal ions such as copper. In this paper we show that similar to various other classes of polyphenols, delphinidin is also capable of causing oxidative degradation of cellular DNA. Lymphocytes were exposed to various concentrations of delphinidin (10, 20, 50 μM) for 1 h and the DNA breakage was assessed using single cell alkaline gel electrophoresis (Comet assay). Inhibition of DNA breakage by several scavengers of reactive oxygen species (ROS) indicated that it is caused by the formation of ROS. Incubation of lymphocytes with neocuproine (a cell membrane permeable Cu(I) chelator) inhibited DNA degradation in intact lymphocytes in a dose dependent manner. Bathocuproine, which is unable to permeate through the cell membrane, did not cause such inhibition. We have further shown that delphinidin is able to degrade DNA in cell nuclei and that such DNA degradation is also inhibited by neocuproine suggesting that nuclear copper is mobilized in this reaction. These results indicate that the generation of ROS possibly occurs through mobilization of endogenous copper ions. The results are in support of our hypothesis that the prooxidant activity of plant polyphenols may be an important mechanism for their anticancer properties

  20. Correlation among Singlet-Oxygen Quenching, Free-Radical Scavenging, and Excited-State Intramolecular-Proton-Transfer Activities in Hydroxyflavones, Anthocyanidins, and 1-Hydroxyanthraquinones.

    Science.gov (United States)

    Nagaoka, Shin-Ichi; Bandoh, Yuki; Nagashima, Umpei; Ohara, Keishi

    2017-10-26

    Singlet-oxygen ( 1 O 2 ) quenching, free-radical scavenging, and excited-state intramolecular proton-transfer (ESIPT) activities of hydroxyflavones, anthocyanidins, and 1-hydroxyanthraquinones were studied by means of laser, stopped-flow, and steady-state spectroscopies. In hydroxyflavones and anthocyanidins, the 1 O 2 quenching activity positively correlates to the free-radical scavenging activity. The reason for this correlation can be understood by considering that an early step of each reaction involves electron transfer from the unfused phenyl ring (B-ring), which is singly bonded to the bicyclic chromen or chromenylium moiety (A- and C-rings). Substitution of an electron-donating OH group at B-ring enhances the electron transfer leading to activation of the 1 O 2 quenching and free-radical scavenging. In 3-hydroxyflavones, the OH substitution at B-ring reduces the activity of ESIPT within C-ring, which can be explained in terms of the nodal-plane model. As a result, the 1 O 2 quenching and free-radical scavenging activities negatively correlate to the ESIPT activity. A catechol structure at B-ring is another factor that enhances the free-radical scavenging in hydroxyflavones. In contrast to these hydroxyflavones, 1-hydroxyanthraquinones having an electron-donating OH substituent adjacent to the O-H---O═C moiety susceptible to ESIPT do not show a simple correlation between their 1 O 2 quenching and ESIPT activities, because the OH substitution modulates these reactions.

  1. Metabolic Characterization of the Anthocyanidin Reductase Pathway Involved in the Biosynthesis of Flavan-3-ols in Elite Shuchazao Tea (Camellia sinensis Cultivar in the Field

    Directory of Open Access Journals (Sweden)

    Lei Zhao

    2017-12-01

    Full Text Available Anthocyanidin reductase (ANR is a key enzyme in the ANR biosynthetic pathway of flavan-3-ols and proanthocyanidins (PAs in plants. Herein, we report characterization of the ANR pathway of flavan-3-ols in Shuchazao tea (Camellia sinesis, which is an elite and widely grown cultivar in China and is rich in flavan-3-ols providing with high nutritional value to human health. In our study, metabolic profiling was preformed to identify two conjugates and four aglycones of flavan-3-ols: (−-epigallocatechin-gallate [(−-EGCG], (−-epicatechin-gallate [(−-ECG], (−-epigallocatechin [(−-EGC], (−-epicatechin [(−-EC], (+-catechin [(+-Ca], and (+-gallocatechin [(+-GC], of which (−-EGCG, (−-ECG, (−-EGC, and (−-EC accounted for 70–85% of total flavan-3-ols in different tissues. Crude ANR enzyme was extracted from young leaves. Enzymatic assays showed that crude ANR extracts catalyzed cyanidin and delphinidin to (−-EC and (−-Ca and (−-EGC and (−-GC, respectively, in which (−-EC and (−-EGC were major products. Moreover, two ANR cDNAs were cloned from leaves, namely CssANRa and CssANRb. His-Tag fused recombinant CssANRa and CssANRb converted cyanidin and delphinidin to (−-EC and (−-Ca and (−-EGC and (−-GC, respectively. In addition, (+-EC was observed from the catalysis of recombinant CssANRa and CssANRb. Further overexpression of the two genes in tobacco led to the formation of PAs in flowers and the reduction of anthocyanins. Taken together, these data indicate that the majority of leaf flavan-3-ols in Shuchazao’s leaves were produced from the ANR pathway.

  2. The Metabolic Fate of Deoxynivalenol and Its Acetylated Derivatives in a Wheat Suspension Culture: Identification and Detection of DON-15-O-Glucoside, 15-Acetyl-DON-3-O-Glucoside and 15-Acetyl-DON-3-Sulfate

    Directory of Open Access Journals (Sweden)

    Clemens Schmeitzl

    2015-08-01

    Full Text Available Deoxynivalenol (DON is a protein synthesis inhibitor produced by the Fusarium species, which frequently contaminates grains used for human or animal consumption. We treated a wheat suspension culture with DON or one of its acetylated derivatives, 3-acetyl-DON (3-ADON, 15-acetyl-DON (15-ADON and 3,15-diacetyl-DON (3,15-diADON, and monitored the metabolization over a course of 96 h. Supernatant and cell extract samples were analyzed using a tailored LC-MS/MS method for the quantification of DON metabolites. We report the formation of tentatively identified DON-15-O-β-D-glucoside (D15G and of 15-acetyl-DON-3-sulfate (15-ADON3S as novel deoxynivalenol metabolites in wheat. Furthermore, we found that the recently identified 15-acetyl-DON-3-O-β-D-glucoside (15-ADON3G is the major metabolite produced after 15-ADON challenge. 3-ADON treatment led to a higher intracellular content of toxic metabolites after six hours compared to all other treatments. 3-ADON was exclusively metabolized into DON before phase II reactions occurred. In contrast, we found that 15-ADON was directly converted into 15-ADON3G and 15-ADON3S in addition to metabolization into deoxynivalenol-3-O-β-D-glucoside (D3G. This study highlights significant differences in the metabolization of DON and its acetylated derivatives.

  3. The anthocyanidin synthase gene from sweetpotato [Ipomoea ...

    African Journals Online (AJOL)

    USER

    2010-06-21

    Jun 21, 2010 ... The tissue expression profiles of IbANS indicated that it could be expressed in all tissues but at different ... al., 1997). Likewise, transcripts of the apple ANS gene are detected ... electrophoresis (EC250-90, E-C Apparatus Corporation) and ... Instruments Inc.) analyses and the RNA samples were stored in a.

  4. Cloning and expression analysis of an anthocyanidin synthase gene ...

    Indian Academy of Sciences (India)

    Structure of AtANS and BcANS1 signal pep- tides was analysed using neural networks (NN) model in http://www.cbs.dtu.dk/services/SignalP/. Based on BcANS1 sequences, primers ANS1D (sense primer: 5 - AAAGGCGGCTATGGATTGGG-3 , antisense primer: 5 - GGCTGAGGGCATTTCGGGTA-3 ) were desig- ned and the ...

  5. Anatomical and biochemical studies of anthocyanidins in flowers of Annagalis monelli L. (Primulaceae) hybrids

    Czech Academy of Sciences Publication Activity Database

    Quintana, A.; Albrechtová, Jana; Griesbach, R. J.; Freyre, R.

    2007-01-01

    Roč. 112, č. 4 (2007), s. 413-421 ISSN 0304-4238 R&D Projects: GA AV ČR(CZ) IAA600110507 Institutional research plan: CEZ:AV0Z60050516 Keywords : flower color * epidermis * structural study Subject RIV: EF - Botanics Impact factor: 0.694, year: 2007

  6. High-performance liquid chromatography for the analytical characterization of anthocyanins in Vaccinium myrtillus L. (bilberry) fruit and food products.

    Science.gov (United States)

    Benvenuti, Stefania; Brighenti, Virginia; Pellati, Federica

    2018-06-01

    Anthocyanins represent the most abundant class of bioactive compounds present in Vaccinium myrtillus L. (bilberry) fruit, conferring it several health-promoting properties. The content of anthocyanins in food products produced from bilberries can be affected by many parameters, making the study of their composition a critical issue. In this ambit, this work was aimed at a comprehensive profiling of anthocyanins in bilberry fruit and derivatives from the Italian Northern Apennines, including jam, juice, and liqueur ("Mirtillino"). Anthocyanins were extracted from the jams by means of a dynamic maceration with acidified methanol, while juice and liqueurs were directly analyzed. The analysis of anthocyanins in the extracts was carried out by means of HPLC-UV/DAD, HPLC-ESI-MS, and MS 2 , under gradient elution. As a comparison, authentic bilberry fruits were analyzed. The total anthocyanin content was in the range 582.4-795.2 mg/100 g (FW) for the fruit, 2.3-234.5 mg/100 g for the jams, 109.2-2252.2 mg/L for the juice, and 27.9-759.3 mg/L for the liqueurs. To deeper investigate the anthocyanin profile of the liqueurs that exhibited a remarkably different composition in comparison with the other products, an authentic bilberry liqueur was prepared in the lab, following a traditional recipe, and monitored weakly by HPLC. The percentage of degradation of 3-O-galactosides and 3-O-arabinosides of bilberry anthocyanidins was found to be higher than that of 3-O-glucosides. The results of this work demonstrated the importance of a suitable and reliable analysis of bilberry fruit and related food products to ensure their genuineness and quality. Graphical abstract Vaccinium myrtillus L. (bilberry) fruit and food products analyzed in this work.

  7. Identification and quantification of anthocyanins in fruits from Neomitranthes obscura (DC.) N. Silveira an endemic specie from Brazil by comparison of chromatographic methodologies.

    Science.gov (United States)

    Gouvêa, Ana Cristina M S; Melo, Armindo; Santiago, Manuela C P A; Peixoto, Fernanda M; Freitas, Vitor; Godoy, Ronoel L O; Ferreira, Isabel M P L V O

    2015-10-15

    Neomitranthes obscura (DC.) N. Silveira is a Brazilian fruit belonging to the Myrtaceae family that contains anthocyanins in the peel and was studied for the first time in this work. Delphinidin-3-O-galactoside, delphinidin-3-O-glucoside, cyanidin-3-O-galactoside, cyanidin-3-O-glucoside, cyanidin-3-O-arabinoside, petunidin-3-O-glucoside, pelargonidin-3-O-glucoside, peonidin-3-O-galactoside, peonidin-3-O-glucoside, cyanidin-3-O-xyloside were separated and identified by LC/DAD/MS and by co-elution with standards. Reliable quantification of anthocyanins in the mature fruits was performed by HPLC/DAD using weighted linear regression model from 0.05 to 50mg of cyaniding-3-O-glucoside L(-1) because it gave better fit quality than least squares linear regression. Good precision and accuracy were obtained. The total anthocyanin content of mature fruits was 263.6 ± 8.2 mg of cyanidin-3-O-glucoside equivalents 100 g(-1) fresh weight, which was in the same range found in literature for anthocyanin rich fruits. Copyright © 2015. Published by Elsevier Ltd.

  8. Inhibitory Effects of Anthocyanins on Secretion of Helicobacter pylori CagA and VacA Toxins

    OpenAIRE

    Sa-Hyun Kim, Min Park, Hyunjun Woo, Nagendran Tharmalingam, Gyusang Lee, Ki-Jong Rhee, Yong Bin Eom, Sang Ik Han, Woo Duck Seo, Jong Bae Kim

    2012-01-01

    Anthocyanins have been studied as potential antimicrobial agents against Helicobacter pylori. We investigated whether the biosynthesis and secretion of cytotoxin-associated protein A (CagA) and vacuolating cytotoxin A (VacA) could be suppressed by anthocyanin treatment in vitro. H. pylori reference strain 60190 (CagA+/VacA+) was used in this study to investigate the inhibitory effects of anthocyanins; cyanidin 3-O-glucoside (C3G), peonidin 3-O-glucoside (Peo3G), pelargonidin 3-O-glucoside (Pe...

  9. LC-MS/MS and UPLC-UV evaluation of anthocyanins and anthocyanidins during rabbiteye blueberry juice processing

    Science.gov (United States)

    Blueberry juice processing includes multiple steps and each affect the chemical composition of the berries, including thermal degradation of anthocyanins. Not from concentrate juice was made by heating and enzyme processing blueberries before pressing followed by ultrafiltration and pasteurization. ...

  10. MUM ENHANCERS are important for seed coat mucilage production and mucilage secretory cell differentiation in Arabidopsis thaliana.

    Science.gov (United States)

    Arsovski, Andrej A; Villota, Maria M; Rowland, Owen; Subramaniam, Rajagopal; Western, Tamara L

    2009-01-01

    Pollination triggers not only embryo development but also the differentiation of the ovule integuments to form a specialized seed coat. The mucilage secretory cells of the Arabidopsis thaliana seed coat undergo a complex differentiation process in which cell growth is followed by the synthesis and secretion of pectinaceous mucilage. A number of genes have been identified affecting mucilage secretory cell differentiation, including MUCILAGE-MODIFIED4 (MUM4). mum4 mutants produce a reduced amount of mucilage and cloning of MUM4 revealed that it encodes a UDP-L-rhamnose synthase that is developmentally up-regulated to provide rhamnose for mucilage pectin synthesis. To identify additional genes acting in mucilage synthesis and secretion, a screen for enhancers of the mum4 phenotype was performed. Eight mum enhancers (men) have been identified, two of which result from defects in known mucilage secretory cell genes (MUM2 and MYB61). Our results show that, in a mum4 background, mutations in MEN1, MEN4, and MEN5 lead to further reductions in mucilage compared to mum4 single mutants, suggesting that they are involved in mucilage synthesis or secretion. Conversely, mutations in MEN2 and MEN6 appear to affect mucilage release rather than quantity. With the exception of men4, whose single mutant exhibits reduced mucilage, none of these genes have a single mutant phenotype, suggesting that they would not have been identified outside the compromised mum4 background.

  11. Ultrasound extracted flavonoids from four varieties of Portuguese red grape skins determined by reverse-phase high-performance liquid chromatography with electrochemical detection.

    Science.gov (United States)

    Novak, Ivana; Janeiro, Patricia; Seruga, Marijan; Oliveira-Brett, Ana Maria

    2008-12-23

    Several flavonoids present in red grape skins from four varieties of Portuguese grapes were determined by reverse-phase high-performance liquid chromatography (RP-HPLC) with electrochemical detection (ECD). Extraction of flavonoids from red grape skins was performed by ultrasonication, and hydrochloric acid in methanol was used as extraction solvent. The developed RP-HPLC method used combined isocratic and gradient elution with amperometric detection with a glassy carbon-working electrode. Good peak resolution was obtained following direct injection of a sample of red grape extract in a pH 2.20 mobile phase. Eleven different flavonoids: cyanidin-3-O-glucoside (kuromanin), delphinidin-3-O-glucoside (myrtillin), petunidin-3-O-glucoside, peonidin-3-O-glucoside, malvidin-3-O-glucoside (oenin), (+)-catechin, rutin, fisetin, myricetin, morin and quercetin, can be separated in a single run by direct injection of sample solution. The limit of detection obtained for these compounds by ECD was 20-90 pg/L, 1000 times lower when compared with photodiode array (PDA) limit of detection of 12-55 ng/L. RP-HPLC-ECD was characterized by an excellent sensitivity and selectivity, and appropriate for the simultaneous determination of these electroactive phenolic compounds present in red grape skins.

  12. Cytotoxicity and Apoptotic Effects of Polyphenols from Sugar Beet Molasses on Colon Carcinoma Cells in Vitro

    Directory of Open Access Journals (Sweden)

    Mingshun Chen

    2016-06-01

    Full Text Available Three polyphenols were isolated and purified from sugar beet molasses by ultrasonic-aid extraction and various chromatographic techniques, and their structures were elucidated by spectral analysis. Cytotoxicity and the molecular mechanism were measured by methyl thiazolyl tetrazolium (MTT assay, flow cytometry, caspase-3 activity assay and Western blot assay. The results showed that gallic acid, cyanidin-3-O-glucoside chloride and epicatechin have cytotoxicity to the human colon, hepatocellular and breast cancer cells. Cyanidin-3-O-glucoside chloride showed its cytotoxicity against various tumor cell lines, particularly against colon cancer Caco-2 cells with half maximal inhibitory concentration (IC50 value of 23.21 ± 0.14 μg/mL in vitro. Cyanidin-3-O-glucoside chloride may be a potential candidate for the treatment of colon cancer. In the mechanism study, cyanidin-3-O-glucoside chloride increased the ratio of cell cycle at G0/G1 phase and reduced cyclin D1 expression on Caco-2 cells. Cyanidin-3-O-glucoside chloride decreased mutant p21 expression, and increased the ratio of Bax/Bcl-2 and the activation of caspase-3 to induce apoptosis.

  13. Anthocyanins in the bracts of Curcuma species and relationship of the species based on anthocyanin composition.

    Science.gov (United States)

    Koshioka, Masaji; Umegaki, Naoko; Boontiang, Kriangsuk; Pornchuti, Witayaporn; Thammasiri, Kanchit; Yamaguchi, Satoshi; Tatsuzawa, Fumi; Nakayama, Masayoshi; Tateishi, Akira; Kubota, Satoshi

    2015-03-01

    Five anthocyanins, delphinidin 3-O-rutinoside, cyanidin 3-O-rutinoside, petunidin 3-O-rutinoside, malvidin 3-O-glucoside and malvidin 3-O-rutinoside, were identified. Three anthocyanins, delphinidin 3-O-glucoside, cyanidin 3-O-glucoside and pelargonidin 3-O-rutinoside, were putatively identified based on C18 HPLC retention time, absorption spectrum, including λmax, and comparisons with those of corresponding standard anthocyanins, as the compounds responsible for the pink to purple-red pigmentation of the bracts of Curcuma alismatifolia and five related species. Cluster analysis based on four major anthocyanins formed two clusters. One consisted of only one species, C. alismatifolia, and the other consisted of five. Each cluster further formed sub-clusters depending on either species or habitats.

  14. Reactive oxygen species scavenging activity of flavone glycosides from Melilotus neapolitana.

    Science.gov (United States)

    Fiorentino, Antonio; D'Abrosca, Brigida; Pacifico, Severina; Golino, Annunziata; Mastellone, Claudio; Oriano, Palma; Monaco, Pietro

    2007-02-28

    One new and six known flavone glycosides were isolated from the MeOH extract of Melilotus neapolitana Ten. The new compound, identified as 7-O-beta-D-glucopyranosyloxy-4',5-dihydroxy-3-[O-alpha-L-rhamnopyranosyl-(1-->6)-3-O-beta-D-glucopyranosyloxy]flavone (1) by 1D and 2D NMR techniques and mass spectra, was isolated along with kaempferol-3-O-rutinoside (2), kaempferol-3-O-glucoside (3), rutin (4), quercetin-3-O-glucoside (5), isorhamnetin-3-O-rutinoside (6), and isorhamnetin-3-O-glucoside (7). The antioxidant and radical scavenging activities of these compounds and the whole crude methanol extract were evaluated. The organic extract can inhibit MDA marker's synthesis by 57%. All the metabolites displayed good reducing power, with the kaempferol (2,3) and isorhamnetin derivatives (6,7) being less active than the corresponding quercetin derivatives 4,5.

  15. Studies on the preparative isolation and stability of seven main anthocyanins from Yan 73 grape.

    Science.gov (United States)

    Tang, Ke; Li, Yang; Han, Yehui; Han, Fuliang; Li, Jiming; Nie, Yao; Xu, Yan

    2014-09-01

    [corrected] Seven anthocyanin monomers of Yan 73 grape were separated using preparative HPLC and identified by UPLC-ESI-MS/MS. The stabilities of the seven isolated anthocyanins to light, temperature and pH were also investigated. Seven anthocyanin monomers were successfully isolated with an Xbridge Prep C18 column on a preparative scale. The pigments delphinidin-3-O-glucoside, malvidin-3-O-acetylglucoside and malvidin-3-O-coumarylglucoside were yielded in a one-step separation by preparative HPLC, with purities up to 99.9%, 91.7% and 95.5%, respectively. The pigments cyanidin-3-O-glucoside, petunidin-3-O-glucoside, peonidin-3-O-glucoside, and malvidin-3-O-glucoside were further purified with another elution method and their purities were all improved up to 99.9%. Monomeric anthocyanin degradation fitted a first-order reaction model. The seven isolated anthocyanins were significantly more stable in the dark than under light. High temperature was also unfavourable for the stability of anthocyanins. The anthocyanins were more stable at lower pH than at higher pH. In addition, among these anthocyanins, delphinidin-3-O-glucoside, malvidin-3-O-acetylglucoside and malvidin-3-O-coumarylglucoside were more susceptible to light, heat, and pH than the others. A simple and clean isolation method of seven anthocyanin monomers from Yan 73 grape was established. The stabilities of the seven anthocyanin monomers to light, temperature and pH were different, but the trends in changes were similar. © 2014 Society of Chemical Industry.

  16. A new kaempferol triglycoside from Fagonia taeckholmiana: cytotoxic activity of its extracts.

    Science.gov (United States)

    Ibrahim, Lamyaa F; Kawashty, Salwa A; El-Hagrassy, Ali M; Nassar, Mahmoud I; Mabry, Tom J

    2008-01-14

    In addition to apigenin, apigenin 7-O-glucoside, kaempferol 3-O-glucoside, kaempferol 3,7-di-O-rhamnoside, quercetin, and quercetin 3-O-glucoside, the methanolic extract of Fagonia taeckholmiana afforded a new compound identified as kaempferol 3-O-beta-l-arabinopyranosyl-(1-->4)-alpha-l-rhamnopyranoside-7-O-alpha-l-rhamnopyranoside. Identification of the isolated compounds was based on chemical and spectroscopic analyses including UV, FABMS, (1)H, (13)C and 2D NMR, and DEPT. The cytotoxic activities of the compounds against several cancer cell lines were determined.

  17. Flavonoids of Helichrysum compactum and their antioxidant and antibacterial activity.

    Science.gov (United States)

    Süzgeç, Sevda; Meriçli, Ali H; Houghton, Peter J; Cubukçu, Bayhan

    2005-03-01

    From the capitula of Helichrysum compactum, the flavonoids apigenin, kaempferol, luteolin, naringenin, 3,5-dihydroxy-6,7,8-trimethoxyflavone, kaempferol-3-O-glucoside, luteolin-7-O-glucoside and luteolin-4',7-di-O-glucoside and from the leafy stems apigenin, kaempferol, luteolin, quercetin, apigenin-7-O-glucoside, luteolin-7-O-glucoside, and quercetin-3-O-glucoside were isolated. Extracts of the capitula of H. compactum show antioxidant activity by inhibition of lipid peroxidation and also show antibacterial activity.

  18. Tandem and sequential multi-enzymatic syntheses

    NARCIS (Netherlands)

    Kim, B.G.; Ahn, J.H.; Sello, G.; Di Gennaro, P.; van Herk, T.; Hartog, A.F.; Wever, R.; Oroz-Guinea, I.; Sánchez-Moreno, I.; García-Junceda, E.; Wu, B.; Szymanski, W.; Feringa, B.L.; Janssen, D.B.; Villo, L.; Kreen, M.; Kudryashova, M.; Metsala, A.; Tamp, S.; Lille, ü.; Pehk, T.; Parve, O.; McClean, K.; Eddowes, P.; Whittall, J.; Sutton, P.W.

    2012-01-01

    This chapter contains sections titled: Production of Isorhamnetin 3-O-Glucoside in Escherichia coli Using Engineered Glycosyltransferase Multienzymatic Preparation of (−)-3-(Oxiran-2-yl)Benzoic Acid Enzymatic Synthesis of Carbohydrates from Dihydroxyacetone and Aldehydes by a One Pot Enzyme Cascade

  19. Inhibitory Effects of Anthocyanins on Secretion of Helicobacter pylori CagA and VacA Toxins

    Science.gov (United States)

    Kim, Sa-Hyun; Park, Min; Woo, Hyunjun; Tharmalingam, Nagendran; Lee, Gyusang; Rhee, Ki-Jong; Eom, Yong Bin; Han, Sang Ik; Seo, Woo Duck; Kim, Jong Bae

    2012-01-01

    Anthocyanins have been studied as potential antimicrobial agents against Helicobacter pylori. We investigated whether the biosynthesis and secretion of cytotoxin-associated protein A (CagA) and vacuolating cytotoxin A (VacA) could be suppressed by anthocyanin treatment in vitro. H. pylori reference strain 60190 (CagA+/VacA+) was used in this study to investigate the inhibitory effects of anthocyanins; cyanidin 3-O-glucoside (C3G), peonidin 3-O-glucoside (Peo3G), pelargonidin 3-O-glucoside (Pel3G), and malvidin 3-O-glucoside (M3G) on expression and secretion of H. pylori toxins. Anthocyanins were added to bacterial cultures and Western blotting was used to determine secretion of CagA and VacA. Among them, we found that C3G inhibited secretion of CagA and VacA resulting in intracellular accumulation of CagA and VacA. C3G had no effect on cagA and vacA expression but suppressed secA transcription. As SecA is involved in translocation of bacterial proteins, the down-regulation of secA expression by C3G offers a mechanistic explanation for the inhibition of toxin secretion. To our knowledge, this is the first report suggesting that C3G inhibits secretion of the H. pylori toxins CagA and VacA via suppression of secA transcription. PMID:23155357

  20. Principal components of phenolics to characterize red Vinho Verde grapes: anthocyanins or non-coloured compounds?

    Science.gov (United States)

    Dopico-García, M S; Fique, A; Guerra, L; Afonso, J M; Pereira, O; Valentão, P; Andrade, P B; Seabra, R M

    2008-06-15

    Phenolic profile of 10 different varieties of red "Vinho Verde" grapes (Azal Tinto, Borraçal, Brancelho, Doçal, Espadeiro, Padeiro de Basto, Pedral, Rabo de ovelha, Verdelho and Vinhão), from Minho (Portugal) were studied. Nine Flavonols, four phenolic acids, three flavan-3-ols, one stilben and eight anthocyanins were determined. Malvidin-3-O-glucoside was the most abundant anthocyanin while the main non-coloured compound was much more heterogeneous: catechin, epicatechin, myricetin-3-O-glucoside, quercetin-3-O-glucoside or syringetin-3-O-glucoside. Anthocyanin contents ranged from 42 to 97%. Principal component analysis (PCA) was applied to analyse the date and study the relations between the samples and their phenolic profiles. Anthocyanin profile proved to be a good marker to characterize the varieties even considering different origin and harvest. "Vinhão" grapes showed anthocyanins levels until twenty four times higher than the rest of the samples, with 97% of these compounds.

  1. Rapid Quantification of Four Anthocyanins in Red Grape Wine by Hydrophilic Interaction Liquid Chromatography/Triple Quadrupole Linear Ion Trap Mass Spectrometry.

    Science.gov (United States)

    Sun, Yongming; Xia, Biqi; Chen, Xiangzhun; Duanmu, Chuansong; Li, Denghao; Han, Chao

    2015-01-01

    The identification and quantification of four anthocyanins (cyanidin-3-O-glucoside, peonidin-3-O-glucoside, delphinidin-3-O-glucoside, and malvidin-3-O-glucoside) in red grape wine were carried out by hydrophilic interaction liquid chromatography/triple quadrupole linear ion trap MS (HILIC/QTrap-MS/MS). Samples were diluted directly and separated on a Merck ZIC HILIC column with 20 mM ammonium acetate solution-acetonitrile mobile phase. Quantitative data acquisition was carried out in the multiple reaction monitoring mode. Additional identification and confirmation of target compounds were performed using the enhanced product ion mode of the linear ion trap. The LOQs were in the range 0.05-1.0 ng/mL. The average recoveries were in the range 94.6 to 104.5%. The HILIC/QTrap-MS/MS platform offers the best sensitivity and specificity for characterization and quantitative determination of the four anthocyanins in red grape wines and fulfills the quality criteria for routine laboratory application.

  2. A protective effect of anthocyanins and xanthophylls on UVB-induced damage in retinal pigment epithelial cells.

    Science.gov (United States)

    Silván, Jose Manuel; Reguero, Marina; de Pascual-Teresa, Sonia

    2016-02-01

    Increased exposure to solar ultraviolet B (UVB) radiation causes oxidative damage that may promote age related macular degeneration (AMD) and other ocular pathologies. This study is aimed to demonstrate the protective effects of some anthocyanins and xanthophylls against the UVB-induced oxidative damage to retinal pigment epithelial (RPE) cells. ARPE-19 cells were treated with 5 μM cyanidin-3-O-glucoside, delphinidin-3-O-glucoside, lutein, zeaxanthin or a mixture of cyanidin-3-O-glucoside:zeaxanthin prior to UVB exposure (500 J m(-2)). Cell viability and mitogen-activated protein kinase (MAPK) phosphorylation were determined by MTT assay and western blot analysis, respectively. Oxidative damage was evaluated by measuring the intracellular reactive oxygen species (ROS). The data showed that UVB irradiation reduces the cell viability to 46% with increasing of intracellular ROS levels and phosphorylation of MAPKs. However, pre-treatment (60 min) with 5 μM cyanidin-3-O-glucoside, lutein or zeaxanthin significantly reduced cellular ROS levels and phosphorylation of MAPKs (JNK1/2 and p38) mediated by UVB irradiation and subsequently increased cell viability. Thus, results show that UVB irradiation is able to induce apoptosis in ARPE-19 cells through oxidative stress; however anthocyanins and xanthophylls pre-treatment can attenuate this damage. This suggests that cyanidin-3-O-glucoside, lutein and zeaxanthin are effective in preventing UVB-induced damage in RPE cells and may be suitable as chemoprotective factors for the prevention of ocular damage. The use of natural dietary antioxidants might reduce ocular oxidative damage caused by UVB radiation.

  3. Separation and purification of polyphenols from red wine extracts using high speed counter current chromatography.

    Science.gov (United States)

    Li, Yuanyuan; Li, Lingxi; Cui, Yan; Zhang, Shuting; Sun, Baoshan

    2017-06-01

    Polyphenols are important compounds of red wine owing to their contribution to sensory properties and antioxidant activities. In this study, high-speed counter-current chromatography (HSCCC) coupled with semi-preparative HPLC was used for large-scale separation and purification of polyphenols from red wine extracts. With the solvent system of hexane-ethyl acetate-water (1-50-50), various oligomeric procyanidins including monomer catechin, epicatechin, dimers B1, B2; phenolic acids including coutaric acid, caftaric acid and other type of polyphenols were largely separated within 370min and most of these compounds presented high yields (0.97mg to 13.79mg) with high purity (90.34% to 98.91%) after the semi-preparative HPLC isolation. Using the solvent system of Methyl tert-Butyl Ether (MTBE) - n-butyl alcohol- acetonitrile-water (1-40-1-50, acidified with 0.01% trifluoroacetic acid (TFA)) by one-step HSCCC of 100mg of the red wine extracts, the major anthocyanins, i.e., malvidin-3-O-glucoside, delphinidin-3-O-glucoside and peonidin-3-O-glucoside, as well as two polymeric proanthocyanidin fractions were successfully separated one another within 320min. The yields of malvidin-3-O-glucoside, delphinidin-3-O-glucoside and peonidin-3-O-glucoside were 12.12mg, 1.78mg and 11.57mg with the purity of 92.74%, 91.03% and 91.21%, respectively. Thiolysis-UPLC analysis indicated that the two polymeric proanthocyanidin fractions presented high purity, with mean degree of polymerization of 7.66±0.12 and 6.20±0.09, respectively. The further experiments on the antioxidant activities by DPPH radical test, FRAP assay and ABTS method showed that all of the isolated procyandins and anthocyanins and the two polymeric proanthocyanidin fractions, with exception of phenolic acids possessed much greater antioxidant activities compared to standard Trolox andl-ascorbic acid (2-14 times). Copyright © 2017 Elsevier B.V. All rights reserved.

  4. Phenolics in the seed coat of wild soybean (Glycine soja) and their significance for seed hardness and seed germination.

    Science.gov (United States)

    Zhou, San; Sekizaki, Haruo; Yang, Zhihong; Sawa, Satoko; Pan, Jun

    2010-10-27

    Hardseededness in annual wild soybean (Glycine soja Sieb. Et Zucc.) is a valuable trait that affects the germination, viability, and quality of stored seeds. Two G. soja ecotypes native to Shandong Province of China have been used to identify the phenolics in the seed coat that correlate with the seed hardness and seed germination. Three major phenolics from the seed coat were isolated and identified as epicatechin, cyanidin 3-O-glucoside, and delphinidin 3-O-glucoside. Of the three phenolics, only the change of epicatechin exhibited a significant positive correlation with the change of hard seed percentages both under different water conditions during seed development and under different gas conditions during seed storage. Epicatechin also reveals a hormesis-like effect on the seed germination of G. soja. Epicatechin is suggested to be functionally related to coat-imposed hardseededness in G. soja.

  5. Effect of variety, processing, and storage on the flavonoid glycoside content and composition of lettuce and endive.

    Science.gov (United States)

    DuPont, M S; Mondin, Z; Williamson, G; Price, K R

    2000-09-01

    Eight varieties of lettuce (Lactuca sativum) and three varieties of endive (Cichorium endivia) were analyzed for flavonoid composition and content. Total flavonoid contents, expressed as units of aglycon for fresh material, were in the ranges of 0.3-229 microg/g for lettuce and 44-248 microg/g for endive. Five quercetin conjugates [quercetin 3-O-galactoside, quercetin 3-O-glucoside, quercetin 3-O-glucuronide, quercetin 3-O-(6-O-malonyl)glucoside, and quercetin 3-O-rhamnoside] and luteolin 7-O-glucuronide were measured in the green-leafed lettuce and an additional two cyanidin conjugates [cyanidin 3-O-glucoside and cyanidin 3-O-[(6-O-malonyl)glucoside

  6. Phytochemical Analysis of Pfaffia glomerata Inflorescences by LC-ESI-MS/MS

    Directory of Open Access Journals (Sweden)

    Daniele F. Felipe

    2014-09-01

    Full Text Available Pfaffia glomerata contains high levels of β-ecdysone, which has shown a range of beneficial pharmacological effects. The present study demonstrated that inflorescences of P. glomerata contain other important bioactive compounds in addition to β-ecdysone. The identification of compounds from inflorescences using liquid chromatography coupled with electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS was performed for the first time. The eight compounds identified were β-ecdysone, flavonoid glycosides such as quercetin-3-O-glucoside, kaempferol-3-O-glucoside and kaempferol-3-O-(6-p-coumaroyl-glucoside, oleanane-type triterpenoid saponins such as ginsenoside Ro and chikusetsusaponin IV, in addition to oleanonic acid and gluconic acid. This study provided information on the phytochemicals contained in P. glomerata inflorescences revealing the potential application of this plant part as raw material for the phytotherapeutic and cosmetic industries.

  7. Liquid chromatography-mass spectrometry identification of anthocyanins of isla oca (Oxalis tuberosa, Mol.) tubers.

    Science.gov (United States)

    Alcalde-Eon, Cristina; Saavedra, Gloria; de Pascual-Teresa, Sonia; Rivas-Gonzalo, Julián C

    2004-10-29

    High-performance liquid chromatography (HPLC)-diode array detection (DAD)-mass spectrometry (MS) techniques have been successfully employed in the identification of the anthocyanins of the coloured tubers of isla oca (Oxalis tuberosa), the second most cultivated tuber in the Andean region. Tubers underwent a pre-treatment step in order to inhibit enzymatic reactions and to obtain a stable powder or "concentrate". This concentrate was dissolved, purified and then analysed. Eight different compounds were found. The major peaks were malvidin glucosides (malvidin 3-O-glucoside and 3,5-O-diglucoside). The rest of the peaks were 3,5-O-diglucosides of petunidin and peonidin, and 3-O-glucosides of delphinidin, petunidin and peonidin. Only malvidin 3-O-acetylglucoside-5-O-glucoside was found as an acylated anthocyanin.

  8. The effect of prefermentative addition of gallic acid and ellagic acid on the red wine color, copigmentation and phenolic profiles during wine aging.

    Science.gov (United States)

    Zhang, Xin-Ke; He, Fei; Zhang, Bo; Reeves, Malcolm J; Liu, Yue; Zhao, Xu; Duan, Chang-Qing

    2018-04-01

    Though non-anthocyanin phenolics normally do not have red color, they affect the red color expression in the copigmentation of red wines. In this study, the influence of prefermentative addition of 300mg/L gallic acid and ellagic acid, as cofactors, on aging dry red wines had been systematically evaluated at the industrial scales from the perspectives of color, phenolic profiles and copigmentation effects of anthocyanins. Red wines made with these two compounds exhibited better color properties than the control, having better CIELAB chromatic parameters. Additionally, significantly higher levels of detectable anthocyanins and copigmented anthocyanin ratio had been observed. Wines with ellagic acid showed better chromatic properties and phenolic profiles than wines with gallic acid, as shown in previous theoretical results. Anti-copigmentation phenomenon was noticed and elucidated. These practical results confirmed that ellagic acid was the better cofactor, and would give more additional guidance for the production of high quality wine. Malvidin-3-O-glucoside (PubChem CID: 443,652); Petunidin-3-O-glucoside (PubChem CID: 443,651); Delphinidin-3-O-glucoside (PubChem CID: 443,650); Peonidin-3-O-glucoside (PubChem CID: 443,654); Ellagic acid (PubChem CID: 5,281,855); Gallic acid (PubChem CID: 370); Quercetin (PubChem CID: 443,654); Caffeic acid (PubChem CID: 689,043); (+)-catechin (PubChem CID: 9064); Vanillic acid (PubChem CID: 8468). Copyright © 2017. Published by Elsevier Ltd.

  9. Red wine alcohol promotes quercetin absorption and directs its metabolism towards isorhamnetin and tamarixetin in rat intestine in vitro

    Science.gov (United States)

    Dragoni, Stefania; Gee, Jennifer; Bennett, Richard; Valoti, Massimo; Sgaragli, Giampietro

    2006-01-01

    Moderate consumption of red wine has been associated with beneficial effects on human health, and this has been attributed to the flavonoid content. Factors that influence the bioavailability of this group of polyphenolic compounds are therefore important. Using the rat cannulated everted jejunal sac technique, we have investigated the effect of alcohol on the intestinal absorption of quercetin and its 3-O-glucoside from red wine. Tissue preparations were incubated in whole or dealcoholised red wine, diluted 1 : 1 with Krebs buffer for 20 min at 37°C, after which the mucosa was removed and processed for HPLC analysis. Tissues exposed to red wine had significantly higher amounts of both quercetin (× 3; P<0.001) and quercetin-3-O-glucoside (× 1.5; P<0.01) associated with them, compared with sacs incubated in the dealcoholised equivalent. In addition, both tamarixetin (T) and isorhamnetin (I), in the mucosal tissue from sacs exposed to the whole wine, were significantly elevated approximately two fold (P<0.05; P<0.01, respectively). Similar results were obtained when sacs were incubated in Krebs buffer containing a mixture of pure quercetin and quercetin-3-O-glucoside with or without alcohol, and, although effects on the apparent absorption of Q and Q-3-G were not so marked, concentrations of the metabolites quercetin-3-O-glucuronide and I were significantly increased by the presence of alcohol (P<0.01 and P<0.001, respectively). It is therefore plausible that the moderate alcohol content of red wine contributes to its beneficial health effects in humans by both increasing the absorption of quercetin and quercetin-3-O-glucoside and by channelling their metabolism towards O-methylation to yield compounds (T and I), which have potential protective effects against cancer and cardiovascular diseases. PMID:16444288

  10. The Beneficial Effect of Anthocyanidin-Rich Vitis vinifera L. Grape Skin Extract on Metabolic Changes Induced by High-Fat Diet in Mice Involves Antiinflammatory and Antioxidant Actions.

    Science.gov (United States)

    da Costa, Gisele França; Santos, Izabelle Barcellos; de Bem, Graziele Freitas; Cordeiro, Viviane Silva Cristino; da Costa, Cristiane Aguiar; de Carvalho, Lenize Costa Reis Marins; Ognibene, Dayane Teixeira; Resende, Angela Castro; de Moura, Roberto Soares

    2017-10-01

    We hypothesized that a polyphenol-rich extract from Vitis vinifera L. grape skin (GSE) may exert beneficial effects on obesity and related metabolic disorders induced by a high-fat diet (HFD). C57/BL6 mice were fed a standard diet (10% fat, control, and GSE groups) or an HFD (60% fat, high fat (HF), and HF + GSE) with or without GSE (200 mg/kg/day) for 12 weeks. GSE prevented weight gain; dyslipidemia; insulin resistance; the alterations in plasma levels of leptin, adiponectin, and resistin; and the deregulation of leptin and adiponectin expression in adipose tissue. These beneficial effects of GSE may be related to a positive modulation of insulin signaling proteins (IR, pIRS, PI3K, pAKT), pAMPK/AMPK ratio, and GLUT4 expression in muscle and adipose tissue. In addition, GSE prevented the oxidative damage, evidenced by the restoration of antioxidant activity and decrease of malondialdehyde and carbonyl levels in muscle and adipose tissue. Finally, GSE showed an anti-inflammatory action, evidenced by the reduced plasma and adipose tissue inflammatory markers (TNF-α, IL-6). Our results suggest that GSE prevented the obesity and related metabolic disorders in HF-fed mice by regulating insulin sensitivity and GLUT4 expression as well as by preventing the oxidative stress and inflammation in skeletal muscle and adipose tissue. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

  11. Effect of flavonols on wine astringency and their interaction with human saliva.

    Science.gov (United States)

    Ferrer-Gallego, Raúl; Brás, Natércia F; García-Estévez, Ignacio; Mateus, Nuno; Rivas-Gonzalo, Julián C; de Freitas, Victor; Escribano-Bailón, M Teresa

    2016-10-15

    The addition of external phenolic compounds to wines in order to improve their sensory quality is an established winemaking practice. This study was aimed at evaluating the effect of the addition of quercetin 3-O-glucoside on the astringency and bitterness of wines. Sensory results showed that the addition of this flavonol to wines results in an increase in astringency and bitterness. Additionally, flavonol-human salivary protein interactions were studied using fluorescence spectroscopy, dynamic light scattering and molecular dynamic simulations (MD). The apparent Stern-Volmer (KsvApp) and the apparent bimolecular quenching constants (kqApp) were calculated from fluorescence spectra. The KsvApp was 12620±390M(-1), and the apparent biomolecular constant was 3.94×10(12)M(-1)s(-1), which suggests that a complex was formed between the human salivary proteins and quercetin 3-O-glucoside. MD simulations showed that the quercetin 3-O-glucoside molecules have the ability to bind to the IB937 model peptide. Copyright © 2016 Elsevier Ltd. All rights reserved.

  12. Chemical Characterization of an Encapsulated Red Wine Powder and Its Effects on Neuronal Cells.

    Science.gov (United States)

    Rocha-Parra, Diego; Chirife, Jorge; Zamora, Clara; de Pascual-Teresa, Sonia

    2018-04-07

    Red wine polyphenols are known for their implications for human health protection, although they suffer from high instability. For this reason, a red wine powder was prepared by freeze-drying encapsulation in maltodextrin/arabic gum matrix, and its composition was determined by means of high-performance liquid chromatography coupled quadrupole time-of-flight mass spectrometry (HPLC-MS-QTOF). More than thirty polyphenols, including anthocyanins, flavanols, flavonols, phenolic acids and stilbenoids, were identified. Some of the main quantified polyphenols were: malvidin-3- O -glucoside, malvidin 3- O -(6″-acetyl-glucose), petunidin-3- O -glucoside, quercetin-3- O -glucuronide, syringenin-3- O -glucoside, epicatechin, gallic acid and syringic acid. The biological activity of this de-alcoholized and encapsulated red wine on human neuroblastoma SH-SY5Y cells was studied. The results showed that the encapsulated red wine powder has active redox properties, as verified by performing reactive oxygen species (ROS) analysis utilizing a neuronal model. This could help explain its action against the neurotoxicity induced by 6-hydroxydopamine (6-OHDA).

  13. Phytochemical profile of a Japanese black-purple rice.

    Science.gov (United States)

    Pereira-Caro, Gema; Watanabe, Shin; Crozier, Alan; Fujimura, Tatsuhito; Yokota, Takao; Ashihara, Hiroshi

    2013-12-01

    Black-purple rice is becoming popular with health conscious food consumers. In the present study, the secondary metabolites in dehulled black-purple rice cv. Asamurasaki were analysed using HPLC-PDA-MS(2). The seeds contained a high concentration of seven anthocyanins (1400 μg/g fresh weight) with cyanidin-3-O-glucoside and peonidin-3-O-glucoside predominating. Five flavonol glycosides, principally quercetin-3-O-glucoside and quercetin-3-O-rutinoside, and flavones were detected at a total concentration of 189 μg/g. The seeds also contained 3.9 μg/g of carotenoids consisting of lutein, zeaxanthin, lycopene and β-carotene. γ-Oryzanol (279 μg/g) was also present as a mixture of 24-methylenecycloartenol ferulate, campesterol ferulate, cycloartenol ferulate and β-sitosterol ferulate. No procyanidins were detected in this variety of black-purple rice. The results demonstrate that the black-purple rice in the dehulled form in which it is consumed by humans contains a rich heterogeneous mixture of phytochemicals which may provide a basis for the potential health benefits, and highlights the possible use of the rice as functional food. Copyright © 2013 Elsevier Ltd. All rights reserved.

  14. Reactive Oxygen Species Scavenging Activity of Flavone Glycosides from Melilotus neapolitana

    Directory of Open Access Journals (Sweden)

    Pietro Monaco

    2007-02-01

    Full Text Available One new and six known flavone glycosides were isolated from the MeOH extract of Melilotus neapolitana Ten. The new compound, identified as 7-O-β-D-gluco-pyranosyloxy-4',5-dihydroxy-3-[O-α-L-rhamnopyranosyl-(1→6-3-O-β-D-glucopyrano-syloxy]flavone (1 by 1D and 2D NMR techniques and mass spectra, was isolated along with kaempferol-3-O-rutinoside (2, kaempferol-3-O-glucoside (3, rutin (4, quercetin-3-O-glucoside (5, isorhamnetin-3-O-rutinoside (6, and isorhamnetin-3-O-glucoside (7. The antioxidant and radical scavenging activities of these compounds and the whole crude methanol extract were evaluated. The organic extract can inhibit MDA marker’s synthesis by 57%. All the metabolites displayed good reducing power, with the kaempferol (2,3 and isorhamnetin derivatives (6,7 being less active than the corresponding quercetin derivatives 4,5.

  15. Chemical Characterization of an Encapsulated Red Wine Powder and Its Effects on Neuronal Cells

    Directory of Open Access Journals (Sweden)

    Diego Rocha-Parra

    2018-04-01

    Full Text Available Red wine polyphenols are known for their implications for human health protection, although they suffer from high instability. For this reason, a red wine powder was prepared by freeze-drying encapsulation in maltodextrin/arabic gum matrix, and its composition was determined by means of high-performance liquid chromatography coupled quadrupole time-of-flight mass spectrometry (HPLC-MS-QTOF. More than thirty polyphenols, including anthocyanins, flavanols, flavonols, phenolic acids and stilbenoids, were identified. Some of the main quantified polyphenols were: malvidin-3-O-glucoside, malvidin 3-O-(6″-acetyl-glucose, petunidin-3-O-glucoside, quercetin-3-O-glucuronide, syringenin-3-O-glucoside, epicatechin, gallic acid and syringic acid. The biological activity of this de-alcoholized and encapsulated red wine on human neuroblastoma SH-SY5Y cells was studied. The results showed that the encapsulated red wine powder has active redox properties, as verified by performing reactive oxygen species (ROS analysis utilizing a neuronal model. This could help explain its action against the neurotoxicity induced by 6-hydroxydopamine (6-OHDA.

  16. Comparison on phenolic compounds and antioxidant properties of cabernet sauvignon and merlot wines from four wine grape-growing regions in China.

    Science.gov (United States)

    Jiang, Bao; Zhang, Zhen-Wen

    2012-07-25

    The antioxidant activities in the Cabernet Sauvignon and Merlot wines from four wine grape-growing regions in China were measured by different analytical assays: 2,2-diphenyl-1-picrylhydrazyl (DPPH·), cupric reducing antioxidant capacity (CUPRAC), superoxide radical-scavenging activity (SRSA) and the contents of total phenols, total flavonoids, total flavanols and total anthocyanins were determined. The results showed that the contents of phenolic compounds and the levels of antioxidant activity in the wine samples greatly varied with cultivar and environmental factors of vine growth. The contents of phenolic compounds and antioxidant activities in Cabernet Sauvignon and Merlot wines from the Yuquanying region of Ningxia were significantly higher than other three regions, followed by the wines from Shacheng region of Hebei, and these parameters were the lowest in Cabernet Sauvignon and Merlot wines from the Changli regions of Hebei and Xiangning region of Shanxi. Taken together, a close relationship between phenolic subclasses and antioxidant activity was observed for the wine samples. Moreover, there were significant discrepancies in the individual phenolic composition and content of four regional Cabernet Sauvignon and Merlot wines, among which the individual phenolic compounds (catechin, epicatechin, cinnamic acid, quercetin-3-O-glucuronide, quercetin-3-O-glucoside, laricitrin-3-O-glucoside and isorhamnetin-3-O-glucoside) revealed a significant correlation (p < 0.05) with the antioxidant capacity in present study, especially for catechin and epicatechin.

  17. Polyphenolic Compositions and Chromatic Characteristics of Bog Bilberry Syrup Wines

    Directory of Open Access Journals (Sweden)

    Shu-Xun Liu

    2015-11-01

    Full Text Available Phenolic compounds determine the color quality of fruit wines. In this study, the phenolic compound content and composition, color characteristics and changes during 6 months of bottle aging were studied in wines fermented with bog bilberry syrup under three different pHs. The total anthocyanins and total phenols were around 15.12–16.23 mg/L and 475.82 to 486.50 mg GAE/L in fresh wines and declined 22%–31% and about 11% in bottle aged wines, respectively. In fresh wines, eight anthocyanins, six phenolic aids and 14 flavonols, but no flavon-3-ols were identified; Malvidin-3-O-glucoside, petunidin-3-O-glucoside and delphinium-3-O-glucoside were the predominant pigments; Chlorogentic acid was the most abundant phenolic acid, and quercetin-3-O-galactoside and myricetin-3-O-galactoside accounted for nearly 90% of the total flavonols. During 6 months of bottle storage, the amounts of all the monomeric anthocyanins and phenolic acids were reduced dramatically, while the glycosidyl flavonols remained constant or were less reduced and their corresponding aglycones increased a lot. The effects of aging on blueberry wine color were described as the loss of color intensity with a dramatic change in color hue, from initial red-purple up to final red-brick nuances, while the pH of the fermentation matrix was negatively related to the color stability of aged wine.

  18. Anthocyanin contents in the seed coat of black soya bean and their anti-human tyrosinase activity and antioxidative activity.

    Science.gov (United States)

    Jhan, J-K; Chung, Y-C; Chen, G-H; Chang, C-H; Lu, Y-C; Hsu, C-K

    2016-06-01

    The seed coat of black soya bean (SCBS) contains high amount of anthocyanins and shows antioxidant and anti-mushroom tyrosinase activities. The objectives of this study were to analyse the anthocyanins in SCBS with different solvents and to find the relationship between anthocyanin profile with anti-human and anti-mushroom tyrosinase activities. SCBS was extracted with hot water, 50 and 80% ethanol, 50 and 80% acetone and 50 and 80% acidified acetone. Total phenol and total flavonoid contents in the extracts were determined. Anthocyanins in the extracts were analysed using HPLC and LC/MS/MS. A genetically engineered human tyrosinase was used to evaluate the anti-tyrosinase potential of the extracts from SCBS. 80% acetone extract from SCBS obtained the highest total phenol, total flavonoid and cyanidin-3-O-glucoside (C3G) contents among all the extracts, whereas the hot water extract showed the lowest antioxidant contents. Three anthocyanin compounds were found in all the extracts from SCBS, and the analysis of HPLC and LC/MS/MS indicated that they were C3G, delphinidin-3-O-glucoside (D3G) and peonidin-3-O-glucoside (P3G). The ratios of C3G (2.84 mg g(-1) ), D3G (0.34 mg g(-1) ) and P3G (0.35 mg g(-1) ) in 80% acidified acetone extract were 76.6, 9.1 and 9.3%, respectively. All the extracts from SCBS possessed anti-human tyrosinase activity. Moreover, a good correlation was found between the anti-human tyrosinase activities and C3G contents in the extracts. Antioxidants in SCBS also possess anti-human and anti-mushroom tyrosinase activities. © 2015 Society of Cosmetic Scientists and the Société Française de Cosmétologie.

  19. Methylation effect on chalcone synthase gene expression determines anthocyanin pigmentation in floral tissues of two Oncidium orchid cultivars.

    Science.gov (United States)

    Liu, Xiao-Jing; Chuang, Yao-Nung; Chiou, Chung-Yi; Chin, Dan-Chu; Shen, Fu-Quan; Yeh, Kai-Wun

    2012-08-01

    The anthocyanin-biosynthetic pathway was studied in flowers of Oncidium Gower Ramsey with yellow floral color and mosaic red anthocyanin in lip crests, sepals and petals, and compared with the anthocyanin biosynthesis in flowers of Oncidium Honey Dollp, a natural somatoclone derived from tissue culture of Gower Ramsey, with a yellow perianth without red anthocyanins in floral tissues. HPLC analysis revealed that the red anthocyanin in lip crests of the Gower Ramsey cultivar comprised peonidin-3-O-glucoside, delphinidin-3-O-glucoside and cyanidin-3-O-glucoside, whereas Honey Dollp was devoid of anthocyanin compounds. Among the five anthocyanin-biosynthetic genes, OgCHS was actively expressed in lip crests of Gower Ramsey flowers, but no transcripts of OgCHS were detected in Honey Dollp floral tissues. Transient expression of OgCHS by bombardment confirmed that recovery of the OgCHS gene expression completed the anthocyanin pathway and produced anthocyanin compounds in lip crests of Honey Dollp flowers. Transcription factor genes regulating anthocyanin biosynthesis showed no distinctive differences in the expression level of OgMYB1, OgbHLH and OgWD40 between the two cultivars. A methylation assay revealed that the promoter of OgCHS was not methylated in Gower Ramsey, while a positive methylation effect was present in the upstream promoter region of OgCHS in Honey Dollp. Overall, our results suggest that the failure of anthocyanin accumulation in Honey Dollp floral tissues may be attributed to inactivation of the OgCHS gene resulting from the epigenetic methylation of 5'-upstream promoter region.

  20. Seasonal accumulation of ultraviolet-B screening pigments in needles of Norway spruce (Picea abies (L.) Karst.)

    International Nuclear Information System (INIS)

    Fischbach, R.J.; Kossmann, B.; Panten, H.; Steinbrecher, R.; Heller, W.; Seidlitz, H.K.; Sandermann, H.; Hertkorn, N.; Schnitzler, J.P.

    1999-01-01

    Conifer needles are highly effective in screening ultraviolet-B radiation (280–320 nm). This ability is mainly attributed to the presence of flavonoids and hydroxycinnamic acids in the epidermal tissue. In two field cabinet experiments with two different clones of Norway spruce we assessed the seasonal accumulation of UV-B screening pigments under near-ambient, and close-to-zero UV-B irradiation. At the beginning of needle development, i.e. in June, kaempferol 3-O-glucoside was the dominant UV-B screening pigment. It was replaced during needle differentiation by the more effective diacylated flavonol glucosides, particulary kaempferol 3-O-(3 , 6 - O-di-p-coumaroyl)-glucoside, which reached highest concentrations in July. In addition to the soluble pool of diacylated flavonol glucoside derivatives, a cell wall-bound UV-B screen in the epidermal cell walls was formed during needle differentiation, consisting mainly of p-coumaric acid and kaempferol 3-O-glucoside. An effect of UV-B radiation on the accumulation of diacylated flavonol glucosides was only observed in 1996 with clone 2, when the concentrations of kaempferol 3-O-(3 , 6 - O-di-p-coumaroyl)-glucoside were significantly higher in July and August under field, and near-ambient than under close-to-zero UV-B irradiance. For wall-bound p-coumaric acid and kaempferol 3-O-glucoside UV-B radiation enhanced the concentrations of these compounds by approximately 20% in relation to the concentrations in close-to-zero UV-B-treated plants in both field cabinet experiments. (author)

  1. Evaluation of the anthocyanin release and health-promoting properties of Pinot Noir grape juices after pulsed electric fields.

    Science.gov (United States)

    Leong, Sze Ying; Burritt, David John; Oey, Indrawati

    2016-04-01

    This study evaluated the health-promoting properties of Pinot Noir juices (Vitis vinifera L.) obtained at different maceration times after pulsed electric fields (PEF) using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and human intestinal Caco-2 cells assays. Juice quality, anthocyanins, total phenolics and vitamin C were also determined. The evaluation of bioprotective capacity of the juice against H2O2-induced oxidative stress in Caco-2 cells was determined using biomarkers for cellular health and integrity: cell viability and lactate dehydrogenase (LDH) leakage. Compared to untreated grape juice, PEF pre-treatment on grapes enhanced the release of the major anthocyanin found in Pinot Noir, i.e. malvidin-3-O-glucoside (+224%). Increase in the content of total phenolic (+61%) and vitamin C (+19%) as well as improvement in the DPPH scavenging activity (+31%) and bioprotective capacity (+25% for cell viability and +30% for LDH leakage) were observed in grape juices following PEF treatment. Bioprotective capacity determined by the cellular biomarkers had significant linear correlations with malvidin-3-O-glucoside content (0.71⩽r⩽0.73) whereas DPPH scavenging activity was not well correlated with malvidin-3-O-glucoside (r=0.30) and total phenolics (r=0.30). Therefore, evaluation of the bioprotective capacities using Caco-2 cell assay performed in this study makes a novel contribution to the current knowledge that demonstrates the capability of PEF technology to produce plant-based foods with better phytochemical composition and exhibiting the capacity to protect cells from oxidative stress. Copyright © 2015 Elsevier Ltd. All rights reserved.

  2. Bioactive components from flowers of Sambucus nigra L. increase glucose uptake in primary porcine myotube cultures and reduce fat accumulation in Caenorhabditis elegans

    DEFF Research Database (Denmark)

    Bhattacharya, Sumangala; Christensen, Kathrine Bisgaard; Olsen, Louise Cathrine Braun

    2013-01-01

    , kaempferol, ferulic acid, p-coumaric acid, and caffeic acid increased GU significantly. FAc was significantly reduced in C. elegans, when treated with elderflower extracts, their fractions and the metabolites naringenin, quercetin-3-O-rutinoside, quercetin-3-O-glucoside, quercetin-3-O-5″-acetylglycoside...... elegans. Bioassay guided chromatographic fractionations of extracts and fractions resulted in the identification of naringenin and 5-O- caffeoylquinic acid exhibiting a significant increase in GU. In addition, phenolic compounds related to those found in elderflowers were also tested, and among these...

  3. Red wine alcohol promotes quercetin absorption and directs its metabolism towards isorhamnetin and tamarixetin in rat intestine in vitro.

    Science.gov (United States)

    Dragoni, Stefania; Gee, Jennifer; Bennett, Richard; Valoti, Massimo; Sgaragli, Giampietro

    2006-04-01

    Moderate consumption of red wine has been associated with beneficial effects on human health, and this has been attributed to the flavonoid content. Factors that influence the bioavailability of this group of polyphenolic compounds are therefore important. Using the rat cannulated everted jejunal sac technique, we have investigated the effect of alcohol on the intestinal absorption of quercetin and its 3-O-glucoside from red wine. Tissue preparations were incubated in whole or dealcoholised red wine, diluted 1 : 1 with Krebs buffer for 20 min at 37 degrees C, after which the mucosa was removed and processed for HPLC analysis. Tissues exposed to red wine had significantly higher amounts of both quercetin (x 3; P wine, were significantly elevated approximately two fold (P moderate alcohol content of red wine contributes to its beneficial health effects in humans by both increasing the absorption of quercetin and quercetin-3-O-glucoside and by channelling their metabolism towards O-methylation to yield compounds (T and I), which have potential protective effects against cancer and cardiovascular diseases.

  4. Stability of Anthocyanins and Their Degradation Products from Cabernet Sauvignon Red Wine under Gastrointestinal pH and Temperature Conditions.

    Science.gov (United States)

    Yang, Ping; Yuan, Chunlong; Wang, Hua; Han, Fuliang; Liu, Yangjie; Wang, Lin; Liu, Yang

    2018-02-07

    This study investigated the stability of wine anthocyanins under simulated gastrointestinal pH and temperature conditions, and further studied the evolution of anthocyanin degradation products through simulated digestive conditions. The aim of this study was to investigate the relation between anthocyanins' structure and their digestive stability. Results showed that a total of 22 anthocyanins were identified in wine and most of these anthocyanins remained stable under simulated gastric digestion process. However, a dramatic concentration decrease happened to these anthocyanins during simulated intestinal digestion. The stability of anthocyanins in digestive process appeared to be related to their structure. The methoxy group in the B-ring enhanced the stability of anthocyanins, whereas hydroxyl group resulted in a reduction of their stability. Acylation decreased the stability of malvidin 3- O -glucoside. Pyruvic acid conjugation enhanced the structural stability of pyranoanthocyanins, whereas acetaldehyde attachment weakened their stability. A commercial malvidin 3- O -glucoside standard was used to investigate anthocyanin degradation products under simulated digestion process, and syringic acid, protocatechuic acid and vanillic acid were confirmed to be the degradation products via anthocyanin chalcone conversion path. Gallic acid, protocatechuic acid, vanillic acid, syringic acid, and p -coumaric acid in wine experienced a significant concentration decrease during digestion process. However, wine model solution revealed that phenolic acids remained stable under gastrointestinal conditions, except gallic acid.

  5. Stability of Anthocyanins and Their Degradation Products from Cabernet Sauvignon Red Wine under Gastrointestinal pH and Temperature Conditions

    Directory of Open Access Journals (Sweden)

    Ping Yang

    2018-02-01

    Full Text Available This study investigated the stability of wine anthocyanins under simulated gastrointestinal pH and temperature conditions, and further studied the evolution of anthocyanin degradation products through simulated digestive conditions. The aim of this study was to investigate the relation between anthocyanins’ structure and their digestive stability. Results showed that a total of 22 anthocyanins were identified in wine and most of these anthocyanins remained stable under simulated gastric digestion process. However, a dramatic concentration decrease happened to these anthocyanins during simulated intestinal digestion. The stability of anthocyanins in digestive process appeared to be related to their structure. The methoxy group in the B-ring enhanced the stability of anthocyanins, whereas hydroxyl group resulted in a reduction of their stability. Acylation decreased the stability of malvidin 3-O-glucoside. Pyruvic acid conjugation enhanced the structural stability of pyranoanthocyanins, whereas acetaldehyde attachment weakened their stability. A commercial malvidin 3-O-glucoside standard was used to investigate anthocyanin degradation products under simulated digestion process, and syringic acid, protocatechuic acid and vanillic acid were confirmed to be the degradation products via anthocyanin chalcone conversion path. Gallic acid, protocatechuic acid, vanillic acid, syringic acid, and p-coumaric acid in wine experienced a significant concentration decrease during digestion process. However, wine model solution revealed that phenolic acids remained stable under gastrointestinal conditions, except gallic acid.

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

    Directory of Open Access Journals (Sweden)

    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.

  7. Postharvest stilbenes and flavonoids enrichment of table grape cv Redglobe (Vitis vinifera L.) as affected by interactive UV-C exposure and storage conditions.

    Science.gov (United States)

    Crupi, Pasquale; Pichierri, Arianna; Basile, Teodora; Antonacci, Donato

    2013-11-15

    Flavonoids and stilbenes are secondary metabolites produced in plants that can play an important health-promoting role. The biosynthesis of these compounds generally increases as a response to biotic or abiotic stress; therefore, in order to achieve as high phenolic accumulation as possible, the interactive effects of storage conditions (temperature and time) and UV-C radiation on polyphenols content in postharvest Redglobe table grape variety were investigated. During a storage time longer than 48h, both cold storage (4°C) and UV-C exposure of almost 3min (2.4kJm(-2)) positively enhanced the content of cis- and trans-piceid (34 and 90μgg(-1) of skin, respectively) together with quercetin-3-O-galactoside and quercetin-3-O-glucoside (15 and 140μgg(-1) of skin, respectively) up to three fold respect to control grape samples. Conversely, catechin was not significantly affected by irradiation and storage treatments. With regard anthocyanins, the highest concentrations of cyanidin-3-O-glucoside and peonidin-3-Oglucoside were observed in Redglobe, stored at both room temperature and 4°C, after 5min (4.1kJm(-2)) of UV-C treatment and 24h of storage. Gathered findings showed that combined postharvest treatments can lead to possible "functional" grapes, within normal conditions of market commercialization, responding to the rising consumers demand to have foods that support and promote health. Copyright © 2013. Published by Elsevier Ltd.

  8. Iron Supply Affects Anthocyanin Content and Related Gene Expression in Berries of Vitis vinifera cv. Cabernet Sauvignon.

    Science.gov (United States)

    Shi, Pengbao; Li, Bing; Chen, Haiju; Song, Changzheng; Meng, Jiangfei; Xi, Zhumei; Zhang, Zhenwen

    2017-02-14

    Anthocyanins are important compounds for red grape and red wine quality, and can be influenced by supply of nutrients such as nitrogen, phosphorus, potassium, zinc, and iron. The present work aims to gain a better understanding of the effect of iron supply on anthocyanins concentration in grape berries. To this end, own-rooted four-year-old Cabernet Sauvignon grapevines ( Vitis vinifera ) were fertigated every three days with 0, 23, 46, 92, and 184 μM iron (Fe) from ferric ethylenediamine di ( o -hydroxyphenylacetic) acid (Fe-EDDHA) in a complete nutrient solution. Fe deficiency or excess generally led to higher concentrations of titratable acidity and skin/berry ratio, and to lower reducing sugar content, sugar/acid ratio, pH, berry weight, and concentration of anthocyanins. Most of the individual anthocyanins detected in this study, except cyanidin-3- O -glucoside, delphinidin-3- O -glucoside, and cyanidin-3- O -(6- O -coumaryl)-glucoside, in moderate Fe treatment (46 μM) grapes were significantly higher than those of other treatments. Genes encoding chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), leucoanthocyanidin dioxygenase (LDOX), and anthocyanin O -methyltransferase (AOMT) exhibited higher transcript levels in berries from plants cultivated with 46 μM Fe compared to the ones cultivated with other Fe concentrations. We suggest that grape sugar content, anthocyanins content, and transcriptions of genes involved in anthocyanin biosynthesis were correlated with Fe supply concentrations.

  9. Black rice (Oryza sativa L.) extracts induce osteoblast differentiation and protect against bone loss in ovariectomized rats.

    Science.gov (United States)

    Jang, Woo-Seok; Seo, Cho-Rong; Jang, Hwan Hee; Song, No-Joon; Kim, Jong-Keun; Ahn, Jee-Yin; Han, Jaejoon; Seo, Woo Duck; Lee, Young Min; Park, Kye Won

    2015-01-01

    Osteoporosis, an age associated skeletal disease, exhibits increased adipogenesis at the expense of osteogenesis from common osteoporotic bone marrow cells. In this study, black rice (Oryza sativa L.) extracts (BRE) were identified as osteogenic inducers. BRE stimulated the alkaline phosphatase (ALP) activity in both C3H10T1/2 and primary bone marrow cells. Similarly, BRE increased mRNA expression of ALP and osterix. Oral administration of BRE in OVX rats prevented decreases in bone density and strength. By contrast, BRE inhibited adipocyte differentiation of mesenchymal C3H10T1/2 cells and prevented increases in body weight and fat mass in high fat diet fed obese mice, further suggesting the dual effects of BRE on anti-adipogenesis and pro-osteogenesis. UPLC analysis identified cyanidin-3-O-glucoside and peonidin-3-O-glucoside as main anti-adipogenic effectors but not for pro-osteogenic induction. In mechanism studies, BRE selectively stimulated Wnt-driven luciferase activities. BRE treatment also induced Wnt-specific target genes such as Axin2, WISP2, and Cyclin D1. Taken together, these data suggest that BRE is a potentially useful ingredient to protect against age related osteoporosis and diet induced obesity.

  10. Experimental design for extraction and quantification of phenolic compounds and organic acids in white "Vinho Verde" grapes.

    Science.gov (United States)

    Dopico-García, M S; Valentão, P; Guerra, L; Andrade, P B; Seabra, R M

    2007-01-30

    An experimental design was applied for the optimization of extraction and clean-up processes of phenolic compounds and organic acids from white "Vinho Verde" grapes. The developed analytical method consisted in two steps: first a solid-liquid extraction of both phenolic compounds and organic acids and then a clean-up step using solid-phase extraction (SPE). Afterwards, phenolic compounds and organic acids were determined by high-performance liquid chromatography (HPLC) coupled to a diode array detector (DAD) and HPLC-UV, respectively. Plackett-Burman design was carried out to select the significant experimental parameters affecting both the extraction and the clean-up steps. The identified and quantified phenolic compounds were: quercetin-3-O-glucoside, quercetin-3-O-rutinoside, kaempferol-3-O-rutinoside, isorhamnetin-3-O-glucoside, quercetin, kaempferol and epicatechin. The determined organic acids were oxalic, citric, tartaric, malic, shikimic and fumaric acids. The obtained results showed that the most important variables were the temperature (40 degrees C) and the solvent (acid water at pH 2 with 5% methanol) for the extraction step and the type of sorbent (C18 non end-capped) for the clean-up step.

  11. Free radical scavenging activity and secondary metabolites from in vitro cultures of Sanicula graveolens.

    Science.gov (United States)

    Cheel, José; Schmeda-Hirschmann, Guillermo; Jordan, Miguel; Theoduloz, Cristina; Rodríguez, Jaime A; Gerth, André; Wilken, Dirk

    2007-01-01

    An in vitro propagation system was developed to obtain shoot and root cultures from the Andean spice Sanicula graveolens (Apiaceae). Propagation of shoots, roots and plantlets was achieved by the temporary immersion system. The free radical scavenging effect of the methanol/water (7:3 v/v) extracts was determined by the discoloration of the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH). Total phenolic, flavonoid, chlorogenic acid (CA) and quercetin 3-O-glucoside content in the samples was assessed by spectrophotometry and DAD-HPLC analysis, respectively. On a dry weight basis, the crude extracts showed total phenolic values ranging from 3.57 to 6.93%, with highest content for the root culture sample. Total flavonoid content ranged from 1.23 to 2.23% and was lower for the root culture. Chlorogenic acid and neochlorogenic acid were identified by TLC in all samples. Highest free radical scavenging effect was observed for the root culture which also presented the highest CA content. Two of the shoot culture samples, with similar IC50 values in the DPPH discoloration assay, also presented close quercetin-3-O-glucoside content.

  12. HPLC-DAD-MS/MS profiling of antioxidant flavonoid glycosides in sea buckthorn (Hippophae rhamnoides L.) seeds.

    Science.gov (United States)

    Arimboor, Ranjith; Arumughan, C

    2012-09-01

    This study was aimed at the chemical profiling of flavonoid glycosides in antioxidant (AO) fractions of sea buckthorn (Hippophae rhamnoides) seed. Seed fractions were evaluated for their DPPH, ABTS, superoxide and hydroxyl radical scavenging, ferric reduction, ferrous chelation and xanthine oxidase inhibitory capacities. HPLC-DAD-ESI-MS/MS analytical conditions for the profiling of seed flavonoids were optimized and the AO-rich fraction was analysed. Quercetin-3-O-rutinoside (5.9%), isorhamnetin-3-O-rutinoside (4.9%) and isorhamnetin-3-O-sophroside-7-O-rhamnoside (3.7%) were found as the major flavonoid glycosides in the fraction. Significant amounts of isorhamnetin-3-O-glucoside (2.8%), 3-O-sophroside-7-O-rhamnosides of quercetin (2.4%) and kaempherol (1.3%), and 3-O-glucoside-7-O-rhamnosides of quercetin (1.1%) and isorhamnetin (1.1%) along with their free forms: isorhamnetin (2.7%), quercetin (1.1%) and kaempherol (0.6%) were also found in the fraction. The identification of flavonoids as the major less polar AO phenolics in the seeds was rationalized by demonstrating the high AO activity of isorhamnetin, quercetin, kaempherol and quercetin-3-O-rutinoside.

  13. Profiling polyphenol composition by HPLC-DAD-ESI/MSn and the antibacterial activity of infusion preparations obtained from four medicinal plants.

    Science.gov (United States)

    Ziani, Borhane E C; Barros, Lillian; Boumehira, Ali Z; Bachari, Khaldoun; Heleno, Sandrina A; Alves, Maria Jose; Ferreira, Isabel C F R

    2018-01-24

    The infusions of Thymus pallescens Noë, Saccocalyx satureioides Coss. et Dur., Ptychotis verticillata Briq. and Limoniastrum guyonianum Boiss. have been used as medicinal remedies for many diseases in Algerian folk medicine. These species have also been well documented as rich sources of phytochemicals, such as phenolic compounds with wide diversified chemical structures, which exhibit far-ranging biological activities. Thus, the phenolic compound profile of the aqueous extracts, obtained by infusing, of the mentioned species was obtained by HPLC-DAD-ESI/MS, and their antibacterial activity was evaluated against clinical isolates. Several phenolic acids were identified and quantified, particularly caffeic acid derivatives along with glycosylated flavonoids. T. pallescens and S. satureioides contain 13 phenolic compounds, where rosmarinic acid was the most abundant phenolic acid present, while L. guyonianum presented myricetin-3-O-glucoside and myricetin-O-rhamnoside as the main compounds among the eight detected molecules. P. verticillata presented a profile of ten phenolic compounds, where 5-O-caffeoylquinic acid was the most abundant phenolic acid, followed by the flavone luteolin-3-O-glucoside. The antibacterial activity of the infusions ranged between 2.5 and 20 mg mL -1 (MIC values), and L. guyonianum showed the highest activity against all of the tested bacteria, Staphylococcus aureus and Pseudomonas aeruginosa being the most sensitive and resistant strains, respectively. Thus, the studied plant species are sources of natural antibacterial substances that can be used to fight against pathogenic microorganisms.

  14. On-line hyphenation of centrifugal partition chromatography and high pressure liquid chromatography for the fractionation of flavonoids from Hippophaë rhamnoides L. berries.

    Science.gov (United States)

    Michel, Thomas; Destandau, Emilie; Elfakir, Claire

    2011-09-09

    Centrifugal Partition Chromatography (CPC), a liquid-liquid preparative chromatography using two immiscible solvent systems, benefits from numerous advantages for the separation or purification of synthetic or natural products. This study presents the on-line hyphenation of CPC-Evaporative Light Scattering Detector (CPC-ELSD) with High Performance Liquid Chromatography-UV (HPLC-UV) for the fractionation of flavonols from a solvent-free microwave extract of sea buckthorn (Hippophaë rhamnoides L., Elaeagnaceae) berries. An Arizona G system was used for the fractionation of flavonoids by CPC and a fused core Halo C18 column allowed the on-line analyses of collected fractions by HPLC. The on-line CPC/HPLC procedure allowed the simultaneous fractionation step at preparative scale combined with the HPLC analyses which provide direct fingerprint of collected fractions. Thus the crude extract was simplified and immediate information on the composition of fractions could be obtained. Furthermore, this methodology reduced the time of post-fractionation steps and facilitated identification of main molecules by Mass Spectrometry (MS). Rutin, isorhamnetin-3-O-rutinoside, isorhamnetin-3-O-glucoside, quercetin-3-O-glucoside, isorhamnetin-rhamnoside, quercetin and isorhamnetin were identified. CPC-ELSD/HPLC-UV could be considered as a high-throughput technique for the guided fractionation of bioactive natural products from complex crude extracts. Copyright © 2011 Elsevier B.V. All rights reserved.

  15. Iron Supply Affects Anthocyanin Content and Related Gene Expression in Berries of Vitis vinifera cv. Cabernet Sauvignon

    Directory of Open Access Journals (Sweden)

    Pengbao Shi

    2017-02-01

    Full Text Available Anthocyanins are important compounds for red grape and red wine quality, and can be influenced by supply of nutrients such as nitrogen, phosphorus, potassium, zinc, and iron. The present work aims to gain a better understanding of the effect of iron supply on anthocyanins concentration in grape berries. To this end, own-rooted four-year-old Cabernet Sauvignon grapevines (Vitis vinifera were fertigated every three days with 0, 23, 46, 92, and 184 μM iron (Fe from ferric ethylenediamine di (o-hydroxyphenylacetic acid (Fe-EDDHA in a complete nutrient solution. Fe deficiency or excess generally led to higher concentrations of titratable acidity and skin/berry ratio, and to lower reducing sugar content, sugar/acid ratio, pH, berry weight, and concentration of anthocyanins. Most of the individual anthocyanins detected in this study, except cyanidin-3-O-glucoside, delphinidin-3-O-glucoside, and cyanidin-3-O-(6-O-coumaryl-glucoside, in moderate Fe treatment (46 μM grapes were significantly higher than those of other treatments. Genes encoding chalcone isomerase (CHI, flavanone 3-hydroxylase (F3H, leucoanthocyanidin dioxygenase (LDOX, and anthocyanin O-methyltransferase (AOMT exhibited higher transcript levels in berries from plants cultivated with 46 μM Fe compared to the ones cultivated with other Fe concentrations. We suggest that grape sugar content, anthocyanins content, and transcriptions of genes involved in anthocyanin biosynthesis were correlated with Fe supply concentrations.

  16. Expression analysis of dihydroflavonol 4-reductase genes in Petunia hybrida.

    Science.gov (United States)

    Chu, Y X; Chen, H R; Wu, A Z; Cai, R; Pan, J S

    2015-05-12

    Dihydroflavonol 4-reductase (DFR) genes from Rosa chinensis (Asn type) and Calibrachoa hybrida (Asp type), driven by a CaMV 35S promoter, were integrated into the petunia (Petunia hybrida) cultivar 9702. Exogenous DFR gene expression characteristics were similar to flower-color changes, and effects on anthocyanin concentration were observed in both types of DFR gene transformants. Expression analysis showed that exogenous DFR genes were expressed in all of the tissues, but the expression levels were significantly different. However, both of them exhibited a high expression level in petals that were starting to open. The introgression of DFR genes may significantly change DFR enzyme activity. Anthocyanin ultra-performance liquid chromatography results showed that anthocyanin concentrations changed according to DFR enzyme activity. Therefore, the change in flower color was probably the result of a DFR enzyme change. Pelargonidin 3-O-glucoside was found in two different transgenic petunias, indicating that both CaDFR and RoDFR could catalyze dihydrokaempferol. Our results also suggest that transgenic petunias with DFR gene of Asp type could biosynthesize pelargonidin 3-O-glucoside.

  17. Bioavailability and health effects of dietary flavonols in man.

    NARCIS (Netherlands)

    Hollman, P.C.H.; Katan, M.B.

    1998-01-01

    Flavonoids are polyphenolic compounds that occur ubiquitously in foods of plant origin. Over 4000 different flavonoids have been described, and they are categorized into flavonols, flavones, catechins, flavanones, anthocyanidins, and isoflavonoids. Flavonoids have a variety of biological effects in

  18. Health effects and bioavailability of dietary flavonols

    NARCIS (Netherlands)

    Hollman, P.C.H.; Katan, M.B.

    1999-01-01

    Flavonoids are polyphenolic compounds that are ubiquitously present in foods of plant origin. Flavonoids are categorised into flavonols, flavones, catechins, flavanones, anthocyanidins, and isoflavonoids. They may have beneficial health effects because of their antioxidant properties and their

  19. The effect of some fixatives on the staining ability of Sorghum bicolor ...

    African Journals Online (AJOL)

    user

    2006-10-20

    Oct 20, 2006 ... The speed of differentiation with acid alcohol and dye fastness on tissue ... Some fixatives act as mordants (Avwioro, 2002). A good example of ... and 13C NMR chemical shifts of a natural anthocyanidin, apigeninidin, using ...

  20. Ultraviolet and environmental stresses involved in the induction and ...

    African Journals Online (AJOL)

    STORAGESEVER

    2008-12-29

    Dec 29, 2008 ... regulating plant development and genes expression. Ultraviolet takes up 7% of ... Fax: 82-33-241-6480. fruits, vegetables, flowers, and other plant tissues or ... Structural classification of general anthocyanidin species (Tahara ...

  1. Antitubercular activity of Arctium lappa and Tussilago farfara extracts and constituents.

    Science.gov (United States)

    Zhao, Jinlian; Evangelopoulos, Dimitrios; Bhakta, Sanjib; Gray, Alexander I; Seidel, Véronique

    2014-08-08

    Arctium lappa and Tussilago farfara (Asteraceae) are two plant species used traditionally as antitubercular remedies. The aim of this study was (i) to screen Arctium lappa and Tussilago farfara extracts for activity against Mycobacterium tuberculosis and (ii) to isolate and identify the compound(s) responsible for this reputed anti-TB effect. The activity of extracts and isolated compounds was determined against Mycobacterium tuberculosis H37Rv using a high throughput spot culture growth inhibition (HT-SPOTi) assay. The n-hexane extracts of both plants, the ethyl acetate extract of Tussilago farfara and the dichloromethane phase derived from the methanol extract of Arctium lappa displayed antitubercular activity (MIC 62.5 μg/mL). Further chemical investigation of Arctium lappa led to the isolation of n-nonacosane (1), taraxasterol acetate (2), taraxasterol (3), a (1:1) mixture of β sitosterol/stigmasterol (4), isololiolide (5), melitensin (6), trans-caffeic acid (7), kaempferol (8), quercetin (9), kaempferol-3-O-glucoside (10). Compounds isolated from Tussilago farfara were identified as a (1:1) mixture of β sitosterol/stigmasterol (4), trans-caffeic acid (7), kaempferol (8), quercetin (9), kaempferol-3-O-glucoside (10), loliolide (11), a (4:1) mixture of p-coumaric acid/4-hydroxybenzoic acid (12), p-coumaric acid (13). All compounds were identified following analyses of their physicochemical and spectroscopic data (MS, (1)H and (13)C-NMR) and by comparison with published data. This is the first report of the isolation of n-nonacosane (1), isololiolide (5), melitensin (6) and kaempferol-3-O-glucoside (10) from Arctium lappa, and of loliolide (11) from Tussilago farfara. Amongst the isolated compounds, the best activity was observed for p-coumaric acid (13) (MIC 31.3 μg/mL or 190.9 μM) alone and in mixture with 4-hydroxybenzoic acid (12) (MIC 62.5 μg/mL). The above results provide for the first time some scientific evidence to support, to some extent, the

  2. New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects.

    Science.gov (United States)

    Abdel Bar, Fatma M

    2015-01-01

    A new chalcanonol glycoside dimer, bis-O-[(I-4') → (II-6')]-α-hydroxyphloretin-2'-O-β-glucoside (1), in addition to six known compounds, namely (-)-epicatechin (2) and (-)-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), β-sitosterol (7) and β-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2'-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers.

  3. Flower color changes in three Japanese hibiscus species: further quantitative variation of anthocyanin and flavonols.

    Science.gov (United States)

    Shimokawa, Satoshi; Iwashina, Tsukasa; Murakami, Noriaki

    2015-03-01

    One anthocyanin and four flavonols were detected from the petals of Hibiscus hamabo, H. tiliaceus and H. glaber. They were identified as cyanidin 3-0- sambubioside, gossypetin 3-O-glucuronide-8-O-glucoside, quercetin 7-O-rutinoside, gossypetin 3-O-glucoside and gossypetin 8-O-glucuronide by UV spectra, LC-MS, acid hydrolysis and HPLC. The flavonoid composition was essentially the same among the petals ofH. hamabo, H. tiliaceus and H. glaber, and there was little quantitative variation, except for cyanidin 3-O-sambubioside, the content of which in the petals ofH. tiliaceus and H. glaber was much higher than in that of H. hamabo. Flower colors of H. tiliaceus and H. glaber change from yellow to red, and that of H. hamabo changes from yellow to orange. These changes were caused by contents of anthocyanin and flavonols, which increased after flowering of H. hamabo, H. tiliaceus and H. glaber.

  4. Oxidation of Wine Polyphenols by Secretomes of Wild Botrytis cinerea Strains from White and Red Grape Varieties and Determination of Their Specific Laccase Activity.

    Science.gov (United States)

    Zimdars, Sabrina; Hitschler, Julia; Schieber, Andreas; Weber, Fabian

    2017-12-06

    Processing of Botrytis cinerea-infected grapes leads to enhanced enzymatic browning reactions mainly caused by the enzyme laccase which is able to oxidize a wide range of phenolic compounds. The extent of color deterioration depends on the activity of the enzymes secreted by the fungus. The present study revealed significant differences in the oxidative properties of secretomes of several B. cinerea strains isolated from five grape varieties. The presumed laccase-containing secretomes varied in their catalytic activity toward six phenolic compounds present in grapes. All strains led to identical product profiles for five of six substrates, but two strains showed deviating product profiles during gallic acid oxidation. Fast oxidation of caffeic acid, ferulic acid, and malvidin 3-O-glucoside was observed. Product formation rates and relative product concentrations were determined. The results reflect the wide range of enzyme activity and the corresponding different impact on color deterioration by B. cinerea.

  5. A new Labdane Diterpene and Other Constituents from Marrubium deserti Noe ex coss.

    Directory of Open Access Journals (Sweden)

    Hocine Dendougui

    2011-01-01

    Full Text Available The phytochemical study of the chloroform soluble part of the hydroalcoholic extract of Marrubium deserti allowed us to describe a new labdane diterpene, 6-dehydroxy-19-acetyl-marrubenol (3 beside three other diterpenes : 19-acetyl-marrubenol (6 , 6-acetyl-marrubenol (7 and 16-epoxy-9-hydroxy-labda-13(16, 14- diene (1. This latter derivative is described for the first time as natural compound. Phytol (2, and three sterols: b -sitosterol (4, stigmasterol (5 and b -sitosterol 3-O-glucoside (8 were also isolated from this species. Structure elucidation of the isolated compounds was accomplished by means of spectroscopic techniques, especially NMR spectroscopy and mass spectrometry.

  6. Flavonóides e triterpenos de Baccharis pseudotenuifolia: bioatividade sobre Artemia salina

    Directory of Open Access Journals (Sweden)

    Moreira Francisco de Paula Madeira

    2003-01-01

    Full Text Available The phytochemical investigation of the chloroformic and methanolic extracts of the Baccharis pseudotenuifolia led to the isolation of triterpenes, steroids and flavonoids. From chloroformic extract were isolated oleanolic acid and alpha-spinasterol while from methanolic extract were isolated the flavonoids: hispidulin, naringenin, 3'-methoxy-luteolin, apigenin, kaempferol, eriodyctiol, aromadendrin, quercetin, 3'-methoxy-quercetin, quercetin-3-O-rhamnoside and quercetin-3-O-glucoside. The structure of these compounds were identified by IR, CG/MS, ¹H and 13C NMR spectral analysis and comparison with literature. In addition, the extracts were evaluated by means of Brine Shrimp Lethality test and the highier activity was observed in the chloroformic extract.

  7. Kaempferol glycosides in the flowers of carnation and their contribution to the creamy white flower color.

    Science.gov (United States)

    Iwashina, Tsukasa; Yamaguchi, Masa-atsu; Nakayama, Masayoshi; Onozaki, Takashi; Yoshida, Hiroyuki; Kawanobu, Shuji; Onoe, Hiroshi; Okamura, Masachika

    2010-12-01

    Three flavonol glycosides were isolated from the flowers of carnation cultivars 'White Wink' and 'Honey Moon'. They were identified from their UV, MS, 1H and 13C NMR spectra as kaempferol 3-O-neohesperidoside, kaempferol 3-O-sophoroside and kaempferol 3-O-glucosyl-(1 --> 2)-[rhamnosyl-(1 --> 6)-glucoside]. Referring to previous reports, flavonols occurring in carnation flowers are characterized as kaempferol 3-O-glucosides with additional sugars binding at the 2 and/or 6-positions of the glucose. The kaempferol glycoside contents of a nearly pure white flower and some creamy white flower lines were compared. Although the major glycoside was different in each line, the total kaempferol contents of the creamy white lines were from 5.9 to 20.9 times higher than the pure white line. Thus, in carnations, kaempferol glycosides surely contribute to the creamy tone of white flowers.

  8. A comparative transcriptome analysis of a wild purple potato and its red mutant provides insight into the mechanism of anthocyanin transformation.

    Directory of Open Access Journals (Sweden)

    Fang Liu

    Full Text Available In this study, a red mutant was obtained through in vitro regeneration of a wild purple potato. High-performance liquid chromatography and Mass spectrometry analysis revealed that pelargonidin-3-O-glucoside and petunidin-3-O-glucoside were main anthocyanins in the mutant and wild type tubers, respectively. In order to thoroughly understand the mechanism of anthocyanin transformation in two materials, a comparative transcriptome analysis of the mutant and wild type was carried out through high-throughput RNA sequencing, and 295 differentially expressed genes (DEGs were obtained. Real-time qRT-PCR validation of DEGs was consistent with the transcriptome date. The DEGs mainly influenced biological and metabolic pathways, including phenylpropanoid biosynthesis and translation, and biosynthesis of flavone and flavonol. In anthocyanin biosynthetic pathway, the analysis of structural genes expressions showed that three genes, one encoding phenylalanine ammonia-lyase, one encoding 4-coumarate-CoA ligase and one encoding flavonoid 3',5'-hydroxylasem were significantly down-regulated in the mutant; one gene encoding phenylalanine ammonia-lyase was significantly up-regulated. Moreover, the transcription factors, such as bZIP family, MYB family, LOB family, MADS family, zf-HD family and C2H2 family, were significantly regulated in anthocyanin transformation. Response proteins of hormone, such as gibberellin, abscisic acid and brassinosteroid, were also significantly regulated in anthocyanin transformation. The information contributes to discovering the candidate genes in anthocyanin transformation, which can serve as a comprehensive resource for molecular mechanism research of anthocyanin transformation in potatoes.

  9. 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.

    Science.gov (United States)

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

    2015-10-19

    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

  10. Elevated CO2 and salinity are responsible for phenolics-enrichment in two differently pigmented lettuces.

    Science.gov (United States)

    Sgherri, Cristina; Pérez-López, Usue; Micaelli, Francesco; Miranda-Apodaca, Jon; Mena-Petite, Amaia; Muñoz-Rueda, Alberto; Quartacci, Mike Frank

    2017-06-01

    Both salt stress and high CO 2 level, besides influencing secondary metabolism, can affect oxidative status of plants mainly acting in an opposite way with salinity provoking oxidative stress and elevated CO 2 alleviating it. The aim of the present work was to study the changes in the composition of phenolic acids and flavonoids as well as in the antioxidant activity in two differently pigmented lettuce cvs (green or red leaf) when submitted to salinity (200 mM NaCl) or elevated CO 2 (700 ppm) or to their combination in order to evaluate how a future global change can affect lettuce quality. Following treatments, the red cv. always maintained higher levels of antioxidant secondary metabolites as well as antioxidant activity, proving to be more responsive to altered environmental conditions than the green one. Overall, these results suggest that the application of moderate salinity or elevated CO 2 , alone or in combination, can induce the production of some phenolics that increase the health benefits of lettuce. In particular, moderate salinity was able to induce the synthesis of the flavonoids quercetin, quercetin-3-O-glucoside, quercetin-3-O-glucuronide and quercitrin. Phenolics-enrichment as well as a higher antioxidant capacity were also observed under high CO 2 with the red lettuce accumulating cyanidin, free chlorogenic acid, conjugated caffeic and ferulic acid as well as quercetin, quercetin-3-O-glucoside, quercetin-3-O-glucuronide, luteolin-7-O-glucoside, rutin, quercitrin and kaempferol. When salinity was present in combination with elevated CO 2 , reduction in yield was prevented and a higher presence of phenolic compounds, in particular luteolin, was observed compared to salinity alone. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  11. FLAVONOIDS AND ANTI-OXIDANT ACTIVITY MEDIATED GASTROPROTECTIVE ACTION OF LEATHERY MURDAH, TERMINALIA CORIACEA (ROXB. WIGHT & ARN. LEAF METHANOLIC EXTRACT IN RATS

    Directory of Open Access Journals (Sweden)

    Mohammed Safwan ALI KHAN

    2017-05-01

    Full Text Available ABSTRACT BACKGROUND Leathery Murdah, Terminalia coriacea (Roxb. Wight & Arn. from family Combretaceae is used in Ayurveda and Siddha traditional systems of medicine to heal ulcers. OBJECTIVE The present study was conducted to assess the gastroprotective effect and understand the fundamental mechanism of action of Leathery Murdah, Terminalia coriacea (Roxb. Wight & Arn. Leaf Methanolic Extract. METHODS The test extract was screened for anti-ulcer activity by Aspirin induced ulcerogenesis in pyloric ligation and ethanol induced gastric ulcers at three doses - 125, 250, and 500 mg/kg, p.o. using Ranitidine 50 mg/kg and Misoprostol 100 μg/kg as standard drug in respective models. Seven parameters were carefully examined, that is, ulcer index, total protein, mucin, catalase, malondialdehyde, and superoxide dismutase levels and histopathology. High Performance Liquid Chromatographic - Ultra Violet profiling and Liquid Chromatography - Mass Spectral analysis of crude Terminalia coriacea leaves methanolic extract were carried out as a part of chemical characterization to identify bioactive compounds. RESULTS All the test doses exhibited significant gastroprotective function, particularly the higher doses demonstrated improved action. The results revealed a significant increase in the levels of catalase, superoxide dismutase, and Mucin with reduction in ulcer index, the levels of total protein, and malondialdehyde. Histopathological observations also illustrated the gastroprotective effect of Terminalia coriacea leaves methanolic extract. CONCLUSION Terminalia coriacea leaves methanolic extract exhibited strong anti-oxidant and anti-secretory activities mediated gastroprotection besides inducing the gastric mucosal production. The observed pharmacological response can be attributed to the flavonoidal compounds namely - Quercetin-3-O-rutinoside, Luteolin-7-O-glucoside, Myricetin hexoside, Quercetin-3-O-glucoside, Isorhamnetin-3-O-rhamnosylglucoside and

  12. Statistical optimization of an RP-HPLC method for the determination of selected flavonoids in berry juices and evaluation of their antioxidant activities.

    Science.gov (United States)

    Ciric, Andrija; Jelikic-Stankov, Milena; Cvijovic, Milica; Djurdjevic, Predrag

    2018-04-01

    An isocratic RP-HPLC method for the separation and identification of selected flavonoids (quercetin, rutin, luteolin-7-O-glucoside, kaempferol and kaempferol-3-O-glucoside) in commercial berry juices (blackcurrant, blueberry, red raspberry and cherry) was developed with the aid of central composite design and response surface methodology. The optimal separation conditions were a mobile phase of 85:15 (% v/v) water-acetonitrile, pH 2.8 (adjusted with formic acid), flow rate 0.5 mL min -1 and column temperature 35°C. The obtained levels of bioflavonoids (mg per 100 mL of juice) were as follows: for quercetin, ca. 0.21-5.12; for kaempferol, ca. 0.05-1.2; for rutin, ca. 0.4-6.5; for luteolin-7-O-glucoside, ca. 5.6-10.2; and for kaempferol-3-O-glucoside, ca. 0.02-0.12. These are considerably lower than the values in fresh fruits. Total phenolic, flavonoid and anthocyanin contents were determined spectrophotometrically. Total flavonoid content varied as follows: blackcurrant > blueberry > red raspberry > cherry. The antioxidant activity of juice extracts (DPPH and ABTS methods) expressed as IC 50 values varied from 8.56 to 14.05 mg L -1 . These values are ~2.5-3 times lower than quercetin, ascorbic acid and Trolox®, but compared with rutin and butylhydroxytoluene, berries show similar or better antioxidant activity by both the DPPH and ABTS methods. Copyright © 2017 John Wiley & Sons, Ltd.

  13. Phenol profiles and antioxidant properties of white skinned grapes and their coloured genotypes during growth

    Directory of Open Access Journals (Sweden)

    Shengyang Niu

    2017-01-01

    Full Text Available Anthocyanins are natural pigments that exhibit a wide range of protective effects with potential benefits for human health related to their antioxidant activities. Grape berries are rich anthocyanins, and these compounds have considerable influence on wine quality. However, these pigments are known to only be present in coloured grape berries. In the present study, we investigated three distinctive grapes, in which only a few reports of mutant strains on the skin colour of the grape berry were reported. Anthocyanin and non-anthocyanin phenolic profiles of grape berry skin, pulp, and seeds at different growth stages were analysed using high performance liquid chromatography of flight mass spectrometry (HPLC-ESI-MS/MS. Meanwhile, grape antioxidant properties were evaluated at growth stages, including the early stage, veraison, and mature stage. The results showed that some anthocyanins contents, such as malvidin 3-O-glucoside, are significantly different between white skin grapes and their corresponding coloured genotypes, with high content in coloured but not in white skin grapes. However, other anthocyanins, such as delphinidin 3-O-glucoside, showed no significant differences between white skin grapes and their corresponding coloured genotypes. Moreover, non-anthocyanin phenolic profiles and antioxidant properties, except cultivars Pinot Blanc and Pinot Noir, showed no significant differences between white skin grapes and their corresponding coloured genotypes at any growth stage, including the pulp and seeds. However, significant differences were noted between different cultivars, for example, white-ciputao and Pinot Noir, Pinot Blanc and Muscat Rouge, and coloured-ciputao and Muscat Blanc, showing that the antioxidant capacity was not always in correlation with skin colour of grape berries.

  14. Determination of Flavonoids and Anthocyanins in Nitraria tangutorum by High Performance Liquid Chromatography Coupled with Tandem Mass Spectrometry.

    Science.gov (United States)

    Zhe, Gao; Ying-Chun, Wang; Yan-Xu, Chang

    2016-01-01

    Using high-performance liquid chromatography coupled with diode array detection and electrospray ionization tandem mass spectrometry (HPLC-DAD-MSn) method, qualitative and quantitative analysis of flavonoids of stems, leaves, fruits and seeds, and anthocyanidin of fresh fruits in Nitraria tangutorum were performed. A total of 14 flavonoid components were identified from the seeds of N. tangutorum including three quercetin derivatives, three kaempferol derivatives, and eight isorhamnetin derivatives. A total of 12, 10, and 7 flavonoid components were identified from leaves, stems, and fruits of N. tangutorum, respectively; all were present in seeds also. The total content of flavonoids in leaves was the highest, up to 42.43 mg/g·dry weight. A total of 12 anthocyanidin components were identified from the fresh fruits of N. tangutorum, belonging to five anthocyanidin. The total content of anthocyanidin in fresh fruits was up to 45.83 mg/100 g· fresh weight, of which the acylated anthocyanidin accounted for 65.7%. The HPLC-DAD-MS(n) method can be operated easily, rapidly, and accurately, and is feasible for qualitative and quantitative analysis of flavone glycosides in N. tangutorum.

  15. Computational study on a puzzle in the biosynthetic pathway of anthocyanin: Why is an enzymatic oxidation/ reduction process required for a simple tautomerization?

    Science.gov (United States)

    Sato, Hajime; Wang, Chao; Yamazaki, Mami; Saito, Kazuki; Uchiyama, Masanobu

    2018-01-01

    In the late stage of anthocyanin biosynthesis, dihydroflavonol reductase (DFR) and anthocyanidin synthase (ANS) mediate a formal tautomerization. However, such oxidation/reduction process requires high energy and appears to be unnecessary, as the oxidation state does not change during the transformation. Thus, a non-enzymatic pathway of tautomerization has also been proposed. To resolve the long-standing issue of whether this non-enzymatic pathway is the main contributor for the biosynthesis, we carried out density functional theory (DFT) calculations to examine this non-enzymatic pathway from dihydroflavonol to anthocyanidin. We show here that the activation barriers for the proposed non-enzymatic tautomerization are too high to enable the reaction to proceed under normal aqueous conditions in plants. The calculations also explain the experimentally observed requirement for acidic conditions during the final step of conversion of 2-flaven-3,4-diol to anthocyanidin; a thermodynamically and kinetically favorable concerted pathway can operate under these conditions.

  16. 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

    Directory of Open Access Journals (Sweden)

    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

  17. A comparison of flavonoid glycosides by electrospray tandem mass spectrometry

    Science.gov (United States)

    March, Raymond E.; Lewars, Errol G.; Stadey, Christopher J.; Miao, Xiu-Sheng; Zhao, Xiaoming; Metcalfe, Chris D.

    2006-01-01

    A comparison is presented of product ion mass spectra of protonated and deprotonated molecules of kaempferol-3-O-glucoside, quercitin-3-O-glucoside (isoquercitrin), quercitin-3-O-galactoside (hyperoin), apigenin-7-O-glucoside, luteolin-7-O-glucoside, genistein-7-O-glucoside, naringenin-7-O-glucoside (prunin), luteolin-4'-O-glucoside, luteolin-6-C-glucoside (homoorientin, known also as isoorientin), apigenin-8-C-glucoside (vitexin), and luteolin-8-C-glucoside (orientin) together with the product ion mass spectrum of deprotonated kaempferol-7-O-glucoside. All isomeric ions were distinguishable on the basis of their product ion mass spectra. For protonated 3-O-, 7-O-, and 4'-O-glycosides at a collision energy of 46-47 eV, homolytic cleavage of the O-glycosidic bond yielded aglycon Y+ ions, whereas in deprotonated 3-O-, 7-O-, and 4'-O-glycosides, heterolytic and homolytic cleavage of the O-glycosidic bond yielded radical aglycon (Y-H)- and aglycon (Y-) ions. In each case, fragmentation of either the glycan or the aglycon or both was observed. For 6-C- and 8-C-glycosides at a collision energy of 46-47 eV, fragmentation was restricted almost exclusively to the glycan. For luteolin-6-C-glucoside, the integrity of the aglycon structure is preserved at the expense of the glycan for which some 30 fragmentations were observed. Breakdown curves were determined as a function of collision energy for protonated and deprotonated luteolin-6-C-glucoside. An attempt has been made to rationalize the product ion mass spectra derived from C-O- and C-C-luteolin glucosides in terms of computed structures that indicate significant intramolecular hydrogen bonding and rotation of the B-ring to form a coplanar luteolin structure. It is proposed that protonated and deprotonated luteolin-6-C-glucoside may afford examples of cooperative interactive bonding that plays a major role in directing fragmentation.

  18. Uncommonly high levels of 3-deoxyanthocyanidins and antioxidant capacity in the leaf sheaths of dye sorghum

    NARCIS (Netherlands)

    Kayode, A.P.P.; Nout, M.J.R.; Linnemann, A.R.; Hounhouigan, J.D.; Berghofer, E.; Siebenhandl-Ehn, S.

    2011-01-01

    Extracts from leaf sheaths of farmers varieties of dye sorghum cultivated and used in Benin as a source of biocolorings were analyzed for their anthocyanidin and phenolic contents, as well as their antioxidant capacity. The aim was to identify and quantify the types of anthocyanin and phenolic

  19. Absorption, metabolism and health effects of dietary flavonoids in man.

    NARCIS (Netherlands)

    Hollman, P.C.H.; Katan, M.B.

    1997-01-01

    Flavonoids are polyphenolic compounds that occur ubiquitously in foods of plant origin. Over 4,000 different flavonoids have been described, and they are categorized into flavonols, flavones, catechins, flavanones, anthocyanidins and isoflavonoids. Flavonoids have a variety of biological effects in

  20. Main: 1GP6 [RPSD[Archive

    Lifescience Database Archive (English)

    Full Text Available urnbull, R.W.D.Welford, I.J.Clifton, A.G.Prescott, C.J.Schofield R.Wilmouth, J.Tu...rnbull, R.Welford, I.Clifton, A.Prescott, C.Schofield Structure And Mechanism Of Anthocyanidin Synthase From

  1. Main: 1GP5 [RPSD[Archive

    Lifescience Database Archive (English)

    Full Text Available .Turnbull, R.W.D.Welford, I.J.Clifton, A.G.Prescott, C.J.Schofield R.Wilmouth, J....Turnbull, R.Welford, I.Clifton, A.Prescott, C.Schofield Structure And Mechanism Of Anthocyanidin Synthase Fr

  2. Enzymatic Processing of Bioactive Glycosides from Natural Sources

    Czech Academy of Sciences Publication Activity Database

    Weignerová, Lenka; Křen, Vladimír

    2010-01-01

    Roč. 295, - (2010), s. 121-146 ISSN 0340-1022 R&D Projects: GA MŠk OC09045 Institutional research plan: CEZ:AV0Z50200510 Keywords : alkaloids * anthocyanidins aroma * cardioglycosides Subject RIV: CC - Organic Chemistry Impact factor: 2.067, year: 2010

  3. Indeks Subjek Volume 31, Tahun 2011

    OpenAIRE

    Volume 31, Tahun 2011, Indeks Subjek

    2012-01-01

    Acid hydrolysis 384Activated carbon 30Adsorption 30Adsorption by active carbon 305Adsorption isotherm 30Afl atoxin B1 168Agroecotourism 139Alcohol 325Alkali 190Ana apple juice 352Analytical Hierarchy Process (AHP) 139Anthocyanidin 93Anthocyanin 93Antibacterial activity 305Antioxidant 290Antiplatelet 52Audit 1Autooxidation 281

  4. Colors of Fruit and Vegetables and 10-Year Incidence of Stroke

    NARCIS (Netherlands)

    Oude Griep, L.M.; Verschuren, W.M.M.; Kromhout, D.; Ocké, M.C.; Geleijnse, J.M.

    2011-01-01

    Background and Purpose—The color of the edible portion of fruits and vegetables reflects the presence of pigmented bioactive compounds, (eg, carotenoids, anthocyanidins, and flavonoids). Which fruit and vegetable color groups contribute most to the beneficial association of fruit and vegetables with

  5. Antioxidant activity and protein-polyphenol interactions in a pomegranate (Punica granatum L.) yogurt.

    Science.gov (United States)

    Trigueros, Lorena; Wojdyło, Aneta; Sendra, Esther

    2014-07-09

    Pomegranate juice (PGJ) is rich in phenolics which are potent antioxidants but also prone to interact with proteins. A yogurt rich in PGJ (40%) made from arils was elaborated (PGY) to determine the antioxidant activity and to estimate the phenolics-proteins interaction during 28 days of cold storage. Juice, yogurts, and protein-free permeates were analyzed for phenolic composition. Yogurt fermentation modified the anthocyanin profile of the initial PGJ, especially the content in cyanidin-3-O-glucoside. During storage, individual anthocyanin content in PGY decreased but it did not modify yogurt color. The analysis of permeates revealed that the degree of phenol-protein interaction depends on the type of phenolic, ellagic acid and dephinidin-3,5-O-diglucoside being the least bound phenolic compounds. The presence of PGJ in yogurt enhanced radical scavenging performance, whereas all the observed ferric reducing power ability of PGY was strictly due to the PGJ present. The 84.73% of total anthocyanins remained bound to proteins at the first day of storage and 90.06% after 28 days of cold storage, revealing the high affinity of anthocyanins for milk proteins.

  6. Protection of color and chemical degradation of anthocyanin from purple corn (Zea mays L.) by zinc ions and alginate through chemical interaction in a beverage model.

    Science.gov (United States)

    Luna-Vital, Diego; Cortez, Regina; Ongkowijoyo, Paulina; Gonzalez de Mejia, Elvira

    2018-03-01

    Anthocyanin-rich purple corn pericarp water extract (PCW) has the potential to be used as a natural pigment in beverages. However, it has a limited shelf-life in aqueous solutions. The aim was to evaluate the effect of zinc ion (Zn 2+ ) and alginate on color and chemical stability of anthocyanins from colored corn (PCW) in a beverage model for 12weeks. PCW was incorporated to Kool-Aid® Invisible™ along with ZnCl 2 and/or alginate. Individual ANC were quantified through HPLC, and color stability was evaluated through the CIE-L*a*b* color system. Complexation between PCW and Zn/alginate was evaluated with fluorescence spectroscopy. The combination of Zn and alginate was the most effective treatment improving the half-life of total ANC concentration (10.4weeks), cyanidin-3-O-glucoside (7.5weeks) and chroma (18.4weeks), compared to only PCW (6.6, 4.5 and 12.7weeks, respectively). Zn and alginate had bimolecular quenching constants (Zn k q : 3.4×10 11 M -1 S -1 and AA k q : 1.0×10 12 M -1 S -1 ) suggesting that fluorescence quenching was binding rather than collisional. Results suggested that Zn/alginate interacted with ANC from purple corn slowing its chemical degradation. Copyright © 2017 Elsevier Ltd. All rights reserved.

  7. Chemical Composition and Immuno-Modulatory Effects of Urtica dioica L. (Stinging Nettle) Extracts.

    Science.gov (United States)

    Francišković, Marina; Gonzalez-Pérez, Raquel; Orčić, Dejan; Sánchez de Medina, Fermín; Martínez-Augustin, Olga; Svirčev, Emilija; Simin, Nataša; Mimica-Dukić, Neda

    2017-08-01

    The purpose of this work was to determine the chemical profile of stinging nettle and to provide an insight into the mechanisms by which it ameliorates the immune response. Qualitative and quantitative liquid chromatography tandem mass spectrometry analyses indicated that phenolic acids (5-O-caffeoylquinic acid as dominant) and flavonol glycosides (rutin, isoquercitrin, and kaempferol 3-O-glucoside) are present in the aerial parts, while lignans (secoisolariciresinol, 9,9'-bisacetyl-neo-olivil and their glucosides) were detected in the root. Herb and root extracts expressed selective inhibition toward cyclooxygenase and lipoxygenase branches in human platelets: root extracts were better at inhibiting thromboxane production, while herb extracts were more specific toward inhibition of 12-lipoxygenase pathway. Stinging nettle extracts mildly increased monocyte chemoattractant protein-1 and growth-related oncogene release from nonstimulated intestinal epithelial cells, stimulating MyD88/NF-κB/p38 signaling, hence preserving the epithelial integrity and enhancing intestinal steady-state defense. Additionally, root extract reduced lipopolysaccharide-induced monocyte chemoattractant protein-1/growth-related oncogene secretion and cyclooxygenase-2 expression in intestinal epithelial cells, thus showing the potential protective effect against tissue damage caused by inflammation processes. These observations suggest that stinging nettle is an interesting candidate for the development of phytopharmaceuticals or dietary supplements for cotreatment of various inflammatory diseases, particularly inflammatory bowel diseases. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

  8. Loss of function of glucocerebrosidase GBA2 is responsible for motor neuron defects in hereditary spastic paraplegia.

    Science.gov (United States)

    Martin, Elodie; Schüle, Rebecca; Smets, Katrien; Rastetter, Agnès; Boukhris, Amir; Loureiro, José L; Gonzalez, Michael A; Mundwiller, Emeline; Deconinck, Tine; Wessner, Marc; Jornea, Ludmila; Oteyza, Andrés Caballero; Durr, Alexandra; Martin, Jean-Jacques; Schöls, Ludger; Mhiri, Chokri; Lamari, Foudil; Züchner, Stephan; De Jonghe, Peter; Kabashi, Edor; Brice, Alexis; Stevanin, Giovanni

    2013-02-07

    Spastic paraplegia 46 refers to a locus mapped to chromosome 9 that accounts for a complicated autosomal-recessive form of hereditary spastic paraplegia (HSP). With next-generation sequencing in three independent families, we identified four different mutations in GBA2 (three truncating variants and one missense variant), which were found to cosegregate with the disease and were absent in controls. GBA2 encodes a microsomal nonlysosomal glucosylceramidase that catalyzes the conversion of glucosylceramide to free glucose and ceramide and the hydrolysis of bile acid 3-O-glucosides. The missense variant was also found at the homozygous state in a simplex subject in whom no residual glucocerebrosidase activity of GBA2 could be evidenced in blood cells, opening the way to a possible measurement of this enzyme activity in clinical practice. The overall phenotype was a complex HSP with mental impairment, cataract, and hypogonadism in males associated with various degrees of corpus callosum and cerebellar atrophy on brain imaging. Antisense morpholino oligonucleotides targeting the zebrafish GBA2 orthologous gene led to abnormal motor behavior and axonal shortening/branching of motoneurons that were rescued by the human wild-type mRNA but not by applying the same mRNA containing the missense mutation. This study highlights the role of ceramide metabolism in HSP pathology. Copyright © 2013 The American Society of Human Genetics. Published by Elsevier Inc. All rights reserved.

  9. Cimicifuga species identification by high performance liquid chromatography-photodiode array/mass spectrometric/evaporative light scattering detection for quality control of black cohosh products

    Science.gov (United States)

    He, Kan; Pauli, Guido F.; Zheng, Bolin; Wang, Huikang; Bai, Naisheng; Peng, Tangsheng; Roller, Marc; Zheng, Qunyi

    2006-01-01

    Black cohosh has become one of the most important herbal products in the U.S. dietary supplements market. It is manufactured from roots and rhizomes of Cimicifuga racemosa (Ranunculaceae). Botanical identification of the raw starting material is a key step in the quality control of black cohosh preparations. The present report summarizes a fingerprinting approach based on HPLC-PDA/MS/ELSD that has been developed and validated using a total of ten Cimicifuga species. These include three North American species, C. racemosa, C. americana, C. rubifolia, and seven Asian species, C. acerina, C. biternat, C. dahurica, C. heracleifolia, C. japonica, C. foetida, and C. simplex. The chemotaxonomic distinctiveness of the HPLC fingerprints allows identification of all ten Cimicifuga species. The triterpene glycosides cimigenol-3-O-arabinoside (3), cimifugin (12), and cimifugin-3-O-glucoside (18) were determined to be suitable species-specific markers for the distinction of C. racemosa from the other Cimicifuga species. In addition to identification, the fingerprint method provided insight into chemical interconversion processes occurring between the diverse triterpene glycosides contained in black cohosh. The reported method has proven its usefulness in the botanical standardization and quality control of black cohosh products. PMID:16515793

  10. Edible Neotropical Blueberries: Antioxidant and Compositional Fingerprint Analysis

    Science.gov (United States)

    DASTMALCHI, KEYVAN; FLORES, GEMA; PETROVA, VANYA; PEDRAZA-PEÑALOSA, PAOLA; KENNELLY, EDWARD J.

    2012-01-01

    Edible blueberry species are well recognized for their potential health benefits. Ericaceae fruits including the North American highbush blueberry (Vaccinium corymbosum L.) and five less common edible blueberry relatives from the New World tropics, Anthopterus wardii Ball, Cavendishia grandifolia Hoerld, Macleania coccoloboides A. C. Sm., Sphyrospermum buxifolium Poepp. & Endl., and Sphyrospermum cordifolium Benth, were investigated for their antioxidant properties and phenolic profiles. The Neotropical berries C. grandifolia and A. wardii exhibited significantly higher DPPH• and ABTS•+ scavenging and iron chelation activities than V. corymbosum. Total phenolic content and HPLC-PDA compositional fingerprint analyses were also carried out. Significant correlations were observed among total phenolic contents, DPPH• and ABTS•+ scavenging, and iron chelation activities. Using HPLC-PDA, the phenolic constituents in the berries were identified as chlorogenic acid, p-coumaric acid, hyperoside, quercetin-3-O-glucoside, isoorientin, isovitexin, orientin and vitexin. Principal components analysis reduced the dimensions of antioxidant and total phenolic data to two components, which accounted for 95% of total variation among the six fruits. Each fruit species formed its own cluster, and therefore the antioxidant profile of each species was shown to be distinct. PMID:21391608

  11. Photoprotection by foliar anthocyanins mitigates effects of boron toxicity in sweet basil (Ocimum basilicum).

    Science.gov (United States)

    Landi, Marco; Guidi, Lucia; Pardossi, Alberto; Tattini, Massimiliano; Gould, Kevin S

    2014-11-01

    Boron (B) toxicity is an important agricultural problem in arid environments. Excess edaphic B compromises photosynthetic efficiency, limits growth and reduces crop yield. However, some purple-leafed cultivars of sweet basil (Ocimum basilicum) exhibit greater tolerance to high B concentrations than do green-leafed cultivars. We hypothesised that foliar anthocyanins protect basil leaf mesophyll from photo-oxidative stress when chloroplast function is compromised by B toxicity. Purple-leafed 'Red Rubin' and green-leafed 'Tigullio' cultivars, grown with high or negligible edaphic B, were given a photoinhibitory light treatment. Possible effects of photoabatement by anthocyanins were simulated by superimposing a purple polycarbonate filter on the green leaves. An ameliorative effect of light filtering on photosynthetic quantum yield and on photo-oxidative load was observed in B-stressed plants. In addition, when green protoplasts from both cultivars were treated with B and illuminated through a screen of anthocyanic protoplasts or a polycarbonate film which approximated cyanidin-3-O-glucoside optical properties, the degree of photoinhibition, hydrogen peroxide production, and malondialdehyde content were reduced. The data provide evidence that anthocyanins exert a photoprotective role in purple-leafed basil mesophyll cells, thereby contributing to improved tolerance to high B concentrations.

  12. Effect of drying of figs (Ficus carica L.) on the contents of sugars, organic acids, and phenolic compounds.

    Science.gov (United States)

    Slatnar, Ana; Klancar, Urska; Stampar, Franci; Veberic, Robert

    2011-11-09

    Fresh figs were subjected to two different drying processes: sun-drying and oven-drying. To assess their effect on the nutritional and health-related properties of figs, sugars, organic acids, single phenolics, total phenolics, and antioxidant activity were determined before and after processing. Samples were analyzed three times in a year, and phenolic compounds were determined using high-performance liquid chromatography coupled with mass spectrometry (HPLC-MS). In figs, monomer sugars predominate, which is important nutritional information, and the content of sugars as well as organic acids in fresh figs was lower than in dried fruits. However, the best sugar/organic acid ratio was measured after the sun-drying process. Analysis of individual phenolic compounds revealed a higher content of all phenolic groups determined after the oven-drying process, with the exception of cyanidin-3-O-rutinoside. Similarly, higher total phenolic content and antioxidant activity were detected after the drying process. With these results it can be concluded that the differences in analyzed compounds in fresh and dried figs are significant. The differences between the sun-dried and oven-dried fruits were determined in organic acids, sugars, chlorogenic acid, catechin, epicatechin, kaempferol-3-O-glucoside, luteolin-8-C-glucoside, and total phenolic contents. The results indicate that properly dried figs can be used as a good source of phenolic compounds.

  13. Antioxidant Capacity, Phenolic Constituents and Toxicity of Hot Water Extract from Red Maple Buds.

    Science.gov (United States)

    Meda, Naamwin R; Poubelle, Patrice E; Stevanovic, Tatjana

    2017-06-01

    The present study reports, for the first time, the results of the antioxidant capacity and the phenolic composition of a hot water extract from red maple buds (RMB), as well as its safety. In this regard and comparatively to antioxidant standards, this extract exhibits a significant antiradical capacity when tested by 2,2-diphenyl-1-picrylhydrazyl (DPPH · ) and anion superoxide trapping assays. High-resolution mass spectrometric and nuclear magnetic resonance analyses permitted to determine for the first time, in red maple species, cyanidin-3-O-glucoside, quercetin-3-O-galactoside, quercetin-3-O-arabinoside, and quercetin. Also, the quantification of individual phenolics by high-performance liquid chromatography method revealed that ginnalin A at 117.0 mg/g is the major compound of RMB hot water extract. Finally, using flow cytometry evaluation, the extract of RMB was determined to have no toxicity neither to cause significant modification of apoptosis process, up to concentration of 100 μg/ml, on human peripheral blood neutrophils. These results allow anticipating various fields of application of RMB water extract. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

  14. Effect of maceration duration on physicochemical characteristics, organic acid, phenolic compounds and antioxidant activity of red wine from Vitis vinifera L. Karaoglan.

    Science.gov (United States)

    Kocabey, N; Yilmaztekin, M; Hayaloglu, A A

    2016-09-01

    Effects of different maceration times (5, 10 and 15 days) on composition, phenolic compounds and antioxidant activities of red wines made from the Vitis vinifera L. Karaoglan grown in Malatya were investigated. Maceration duration changed some chemical constituents and color of Karaoglan red wines. A linear relationship was observed between antioxidant activity of wine and maceration duration. Major organic acid was tartaric acid which was at the highest concentration in wine macerated for 10 days. A total of 25 phenolic compounds was determined in wine samples. Within these phenolics; procyanidin B2, trans -caftaric acid, gallic acid, trans -caffeic acid, (+) catechin, (-) epicatechin and quercetin-3- O -glucoside were the most abundant phenolics regardless of maceration duration. In general, extended maceration duration resulted in increase in the concentration of phenolic compounds, reflecting the antioxidant activities of wine. In conclusion, the highest concentrations of total and individual phenolic compounds as well as antioxidant activities were found in wines macerated for 15 days.

  15. Characterization of a Vitis vinifera cv. Cabernet Sauvignon 3',5'-O-methyltransferase showing strong preference for anthocyanins and glycosylated flavonols.

    Science.gov (United States)

    Lücker, Joost; Martens, Stefan; Lund, Steven T

    2010-09-01

    At ripening initiation in red grapevine (Vitis vinifera) berries, the exocarp turns color from green to red and then to purple due to the accumulation and extent of methylation of anthocyanins. The accumulation of transcripts encoding an O-methyltransferase was recently shown to be closely correlated with the onset of ripening and the degree of blue/purple pigmentation in grapevine berries; however, the biochemical function of this gene has remained uncharacterized. In this study, an O-methyltransferase cDNA that showed a distinct expression pattern when compared to closely related sequences was expressed in Escherichia coli and enzyme assays were carried out with a broad array of anthocyanin and other flavonoid substrates. We demonstrate that this enzyme carries out 3',5'-O-methylation of anthocyanins and flavonol compounds in vitro, which are known to be present in grape berries, with a preference for glycosylated substrates. The highest relative specific activity for the enzyme was found with delphinidin 3-O-glucoside as substrate. The enzyme is not able to methylate flavan type skeletons with chiral centers, such as either catechins or dihydroquercetin. The enzyme showed negligible specific activity for caffeoyl-CoA, compared to flavonol and anthocyanin substrates. Phylogenetic analysis of the O-methyltransferase suggests that it may be a member of a distinct subclass of Type 2 bivalent metal-dependent S-adenosyl-methionine O-methyltransferases. (c) 2010. Published by Elsevier Ltd. All rights reserved.

  16. Identification of Phenolic Compounds in Red and Green Pistachio (Pistacia vera L.) Hulls (Exo- and Mesocarp) by HPLC-DAD-ESI-(HR)-MS(n).

    Science.gov (United States)

    Erşan, Sevcan; Güçlü Üstündağ, Özlem; Carle, Reinhold; Schweiggert, Ralf M

    2016-07-06

    Phenolic constituents of the nonlignified red and green pistachio hulls (exo- and mesocarp) were assessed by HPLC-DAD-ESI-MS(n) as well as by HR-MS. A total of 66 compounds was identified in the respective aqueous methanolic extracts. Among them, gallic acid, monogalloyl glucoside, monogalloyl quinic acid, penta-O-galloyl-β-d-glucose, hexagalloyl hexose, quercetin 3-O-galactoside, quercetin 3-O-glucoside, quercetin 3-O-glucuronide, and (17:1)-, (13:0)-, and (13:1)-anacardic acids were detected at highest signal intensity. The main difference between red and green hulls was the presence of anthocyanins in the former ones. Differently galloylated hydrolyzable tannins, anthocyanins, and minor anacardic acids were identified for the first time. Pistachio hulls were thus shown to be a source of structurally diverse and potentially bioactive phenolic compounds. They therefore represent a valuable byproduct of pistachio processing having potential for further utilization as raw material for the recovery of pharmaceutical, nutraceutical, and chemical products.

  17. Phenolic and triterpenoid composition and inhibition of α-amylase of pistachio kernels (Pistacia vera L.) as affected by rootstock and irrigation treatment.

    Science.gov (United States)

    Noguera-Artiaga, Luis; Pérez-López, David; Burgos-Hernández, Armando; Wojdyło, Aneta; Carbonell-Barrachina, Ángel A

    2018-09-30

    The current water scarcity forces farmers to adopt new irrigation strategies to save water without jeopardizing the fruit yield and quality. In this study, the influence of 3 regulated deficit irrigation (RDI) treatments and 3 rootstocks on the functional quality of pistachios were studied. The functional parameters studied included, polyphenols, triterpenoids, and inhibition of α-amylase. The results showed that P. terebinthus and P. atlantica rootstocks led to pistachio kernels with higher contents of polyphenols and triterpenoids (mainly betulinic acid with 111 and 102 µg g -1 , respectively) than pistachios obtained using P. integerrima rootstock (81 µg g -1 ). On the other hand, the use of moderate RDI (T1 treatment) increased the total content of polyphenols (∼10%), quercetin-O-galloyl-hexoside (∼15%), keampferol-3-O-glucoside (∼19%), and polymeric procyanidins (∼20%), as compared to the control trees, resulting in pistachios with a better functional profile, lower economic cost and with a lesser environmental impact. Copyright © 2018 Elsevier Ltd. All rights reserved.

  18. Evaluation of the nutraceutical, antioxidant and cytoprotective properties of ripe pistachio (Pistacia vera L., variety Bronte) hulls.

    Science.gov (United States)

    Barreca, Davide; Laganà, Giuseppina; Leuzzi, Ugo; Smeriglio, Antonella; Trombetta, Domenico; Bellocco, Ersilia

    2016-04-01

    Every year tons of pistachio hulls are separated and eliminated, as waste products, from pistachio seeds. In this study the hulls of ripe pistachios were extracted with two organic solvents (ethanol and methanol) and characterized for phenolic composition, antioxidant power and cytoprotective activity. RP-HPLC-DAD-FLU separation enabled us to identify 20 derivatives, including and by far the most abundant gallic acid, 4-hydroxybenzoic acid, protocatechuic acid, naringin, eriodictyol-7-O-glucoside, isorhamnetin-7-O-glucoside, quercetin-3-O-rutinoside, isorhamnetin-3-O-glucoside and catechin. Methanol extraction gave the highest yields for all classes of compounds and presented a higher scavenging activity in all the antioxidant assays performed. The same was found for cytoprotective activity on lymphocytes, lipid peroxidation and protein degradation. These findings highlight the strong antioxidant and cytoprotective activity of the extract components, and illustrate how a waste product can be used as a source of nutraceuticals to employ in manufacturing industry. Copyright © 2015 Elsevier Ltd. All rights reserved.

  19. Identification of Characteristic Phenolic Constituents in Mousouchiku Extract Used as Food Additives.

    Science.gov (United States)

    Yoshimura, Morio; Ochi, Keisuke; Sekiya, Hiroshi; Tamai, Eiji; Maki, Jun; Tada, Atsuko; Sugimoto, Naoki; Akiyama, Hiroshi; Amakura, Yoshiaki

    2017-01-01

    Mousouchiku extract is prepared from the bamboo-sheath of Phyllostachys heterocycla MITF. (Poaceae), and is registered as a food manufacturing agent in the List of Existing Food Additives in Japan. This study describes the chromatographic evaluation of characteristic components of this extract to obtain the chemical data needed for standardized specifications. We isolated 12 known compounds from this extract: 5-hydroxymethyl-2-furfural, 4-hydroxybenzoic acid, trans-p-coumaric acid, trans-ferulic acid, N,N'-diferuloylputrescine, 4'-hydroxypropiophenone, β-arbutin, tachioside, isotachioside, 3,4'-dihydroxypropiophenone 3-O-glucoside, koaburaside, and (+)-lyoniresinol 9'-O-glucoside. Moreover, a new propiophenone glycoside, propiophenone 4'-O-(6-β-D-xylosyl)-β-D-glucoside (propiophenone 4'-O-primeveroside), was isolated. The structure of each isolated compound was elucidated based on NMR and MS data or direct HPLC comparisons with authentic samples. Among the isolates, (+)-lyoniresinol 9'-O-glucoside was found to be the major ingredients of the extract as observed using HPLC analysis. However, 2,6-dimethoxy-1,4-benzoquinone, which is considered the main constituent of mousouchiku extract, was only detected as a trace constituent and not isolated in this study.

  20. Transgenic Wheat Expressing a Barley UDP-Glucosyltransferase Detoxifies Deoxynivalenol and Provides High Levels of Resistance to Fusarium graminearum.

    Science.gov (United States)

    Li, Xin; Shin, Sanghyun; Heinen, Shane; Dill-Macky, Ruth; Berthiller, Franz; Nersesian, Natalya; Clemente, Thomas; McCormick, Susan; Muehlbauer, Gary J

    2015-11-01

    Fusarium head blight (FHB), mainly caused by Fusarium graminearum, is a devastating disease of wheat that results in economic losses worldwide. During infection, F. graminearum produces trichothecene mycotoxins, including deoxynivalenol (DON), that increase fungal virulence and reduce grain quality. Transgenic wheat expressing a barley UDP-glucosyltransferase (HvUGT13248) were developed and evaluated for FHB resistance, DON accumulation, and the ability to metabolize DON to the less toxic DON-3-O-glucoside (D3G). Point-inoculation tests in the greenhouse showed that transgenic wheat carrying HvUGT13248 exhibited significantly higher resistance to disease spread in the spike (type II resistance) compared with nontransformed controls. Two transgenic events displayed complete suppression of disease spread in the spikes. Expression of HvUGT13248 in transgenic wheat rapidly and efficiently conjugated DON to D3G, suggesting that the enzymatic rate of DON detoxification translates to type II resistance. Under field conditions, FHB severity was variable; nonetheless, transgenic events showed significantly less-severe disease phenotypes compared with the nontransformed controls. In addition, a seedling assay demonstrated that the transformed plants had a higher tolerance to DON-inhibited root growth than nontransformed plants. These results demonstrate the utility of detoxifying DON as a FHB control strategy in wheat.

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

    Directory of Open Access Journals (Sweden)

    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.

  2. Preharvest application of oxalic acid improves quality and phytochemical content of artichoke (Cynara scolymus L.) at harvest and during storage.

    Science.gov (United States)

    Martínez-Esplá, Alejandra; García-Pastor, María Emma; Zapata, Pedro Javier; Guillén, Fabián; Serrano, María; Valero, Daniel; Gironés-Vilaplana, Amadeo

    2017-09-01

    In this study the effect of oxalic acid (OA) treatment of artichoke plants (Cynara scolymus L.) on head artichoke development and on artichokes quality parameters (weight loss, firmness, and color), respiration rate, antioxidant activity and phenolics (measured by Folin Ciocalteu and HPLC-DAD-ESI/MS n ) at harvest and during storage for 21days at 2°C was evaluated. OA treatment increased the percentage of the first class artichokes although no significant effect was found in artichoke developmental process. OA-treatment reduced the respiration rate of artichokes and led to higher total hydrosoluble antioxidant activity and total phenolics and hydroxycinnamics and luteolins concentration both at harvest and during cold storage. In addition, luteolin 7-O-glucuronide 3-O-glucoside was identified for the first time in artichoke. Thus, it can be concluded that OA preharvest treatment could be a natural and useful tool to delay the artichoke postharvest senescence and improve the reported health-beneficial properties of artichokes consumption. Copyright © 2017 Elsevier Ltd. All rights reserved.

  3. Unlike Quercetin Glycosides, Cyanidin Glycoside in Red Leaf Lettuce Responds More Sensitively to Increasing Low Radiation Intensity before than after Head Formation Has Started

    Science.gov (United States)

    2014-01-01

    This study investigated the effect of low-level photosynthetic photon flux density (PPFD; 43–230 μmol m–2 s–1) on the major phenolic compounds of red leaf lettuce in three growth stages, before, during, and after head formation, using HPLC-DAD-ESI-MS2 and evaluating via multiple regression analysis. Generally, the light-related increase of flavonoid glycosides was structure and growth stage-dependent. In detail, an interaction was detected between plant age and PPFD regarding cyanidin-3-O-(6″-O-malonyl)-glucoside concentration: the increase was strongest before head formation. The relationship between PPFD and quercetin-3-O-(6″-O-malonyl)-glucoside concentration was linear, whereas the increase of quercetin-3-O-glucoside and -3-O-glucuronide concentrations abated with increasing PPFD. Independent of growth stage, the caffeic acid derivatives concentration was not related to PPFD. All major phenolic compounds decreased with plant age. These results show the differential regulation of cyanidin, quercetin, and caffeic acid derivatives in lettuce, although closely connected biosynthetically, and emphasize the importance of ontogeny in the study of plant physiology. PMID:24382136

  4. Antioxidant Constituents of Cotoneaster melanocarpus Lodd.

    Directory of Open Access Journals (Sweden)

    Adelheid H. Brantner

    2013-10-01

    Full Text Available The aim of this study was the evaluation of the antioxidant capacity of Cotoneaster melanocarpus Lodd. and the identification of antioxidant active constituents of this plant. C. melanocarpus Lodd. is a shrub indigenous to Mongolia and used in Traditional Mongolian Medicine as a styptic. Before extraction, the plant material was separated into three parts: young sterile shoots, older stems and leaves. All these parts were extracted with water, methanol, ethyl acetate, dichloromethane and hexane, successively. The methanolic extract of the sterile shoots showed the highest antioxidant activity in the DPPH (2,2-diphenyl-1-picrylhydrazyl radical scavenging assay (IC50 30.91 ± 2.97 µg/mL. This active extract was further analyzed with chromatographic methods. TLC fingerprinting and HPLC indicated the presence of the flavonol glycosides quercetin-3-O-rutinoside (rutin, quercetin-3-O-galactoside (hyperoside and quercetin-3-O-glucoside (isoquercetin, ursolic acid as well as chlorogenic acid, neochlorogenic acid and cryptochlorogenic acid. The findings were substantiated with LC-MS. All identified compounds have antioxidant properties and therefore contribute to the radical scavenging activity of the whole plant.

  5. Optimisation of ultrasonic-assisted extraction of phenolic compounds, antioxidants, and anthocyanins from sugar beet molasses.

    Science.gov (United States)

    Chen, Mingshun; Zhao, Yi; Yu, Shujuan

    2015-04-01

    Response surface methodology was used to optimise experimental conditions for ultrasonic-assisted extraction (UAE) of functional components from sugar beet molasses. The central composite design (CCD) was used for the optimisation of extraction parameters in terms of total phenolic contents, antioxidant activities and anthocyanins. Result suggested the optimal conditions obtained by RSM for UAE from sugar beet molasses were as follows: HCl concentration 1.55-1.72 mol/L, ethanol concentration 57-63% (v/v), extraction temperature 41-48 °C, and extraction time 66-73 min. In the optimal conditions, the experimental total phenolic contents were 17.36 mg GAE/100mL, antioxidant activity was 16.66 mg TE/g, and total anthocyanins were 31.81 mg/100g of the sugar beet molasses extract, which were well matched the predicted values. Teen compounds, i.e. gallic acid, vanillin, hydroxybenzoic acid, syringic acid, cyanidin-3-O-rutinoside, cyanidin-3-O-glucoside, catechin, delphinidin-3-O-rutinoside, delphinidin-3-O-glucuronide and ferulic acid were determined by HPLC-DAD-MS/MS in sugar beet molasses. Copyright © 2014 Elsevier Ltd. All rights reserved.

  6. Optimization of microwave-assisted extraction for anthocyanins, polyphenols, and antioxidants from raspberry (Rubus Coreanus Miq.) using response surface methodology.

    Science.gov (United States)

    Teng, Hui; Lee, Won Young; Choi, Yong Hee

    2013-09-01

    Anthocyanins (Acys), polyphenols, and antioxidants were extracted from raspberry (Rubus Coreanus Miq.) using a highly efficient microwave-assisted extraction technique. Different solvents, including methanol, ethanol, and acetone, were tested. The colors of the extracts varied from light yellow to purple red or dark red. SEM and other nutrient analyses verified that ethanol was the most favorable medium for the microwave-assisted extraction of raspberry due to its high output and low toxicity. Effects of process parameters, including microwave power, irradiation time, and solvent concentration, were investigated through response surface methodology. Canonical analysis estimated that the highest total Acys content, total polyphenols content, and antioxidant activity of raspberry were 17.93 mg cyanidin-3-O-glucoside equivalents per gram dry weight, 38.57 mg gallic acid equivalents per gram dry weight, and 81.24%, respectively. The polyphenol compositions of raspberry extract were identified by HPLC with diode array detection, and nine kinds of polyphenols were identified and quantified, revealing that chlorogenic acid, syringic acid, and rutin are the major polyphenols contained in raspberry fruits. Compared with other fruits and vegetables, raspberry contains higher Acy and polyphenol contents with stronger antioxidant activity, suggesting that raspberry fruits are a good source of natural food colorants and antioxidants. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  7. Pink berry grape (Vitis vinifera L.) characterization: Reflectance spectroscopy, HPLC and molecular markers.

    Science.gov (United States)

    Rustioni, Laura; De Lorenzis, Gabriella; Hârţa, Monica; Failla, Osvaldo

    2016-01-01

    Color has a fundamental role for the qualitative evaluation and cultivar characterization of fruits. In grape, a normally functional pigment biosynthesis leads to the accumulation of a high quantity of anthocyanins. In this work, 28 Vitis vinifera L. cultivars accumulating low anthocyanins in berries were studied to characterize the biosynthetic dysfunctions in both a phenotypic and genotypic point of view. Reflectance spectroscopy, HPLC profiles and molecular markers related to VvMybA1 and VvMybA2 genes allowed a detailed description of the pigment-related characteristics of these cultivars. Data were consistent concerning the heterozygosity of the non-functional allele in both investigated genes, resulting in a low colored phenotype as described by reflectance. However, the variability in berry colour among our samples was not fully explained by MybA locus, probably due to specific interferences among the biosynthetic pathways, as suggested by the anthocyanin profile variations detected among our samples. The results presented in this work confirmed the importance of the genetic background: grapes accumulating high levels of cyanidin-3-O-glucosides (di-substituted anthocyanin) are generally originated by white cultivar retro-mutations and they seem to preserve the anomalies in the flavonoid hydroxylases enzymes which negatively affect the synthesis of tri-substituted anthocyanins. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

  8. Profile of the Phenolic Compounds of Rosa rugosa Petals

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    Andrzej Cendrowski

    2017-01-01

    Full Text Available Rosa rugosa petals are a rich source of phenolic compounds, which determined their antioxidant properties. The aim of this study was to determine the polyphenolic composition of not processed petals of Rosa rugosa collected from the commodity crops and to determine the variability of the contained therein polyphenols between harvesting seasons. Twenty polyphenols were identified by UPLC-ESI-MS. The main fraction of polyphenols was ellagitannins, which are 69 to 74% of the total polyphenols of the petals. In the petals of Rosa rugosa, four anthocyanins have been identified: cyanidin 3,5-di-O-glucoside, peonidin 3-O-sophoroside, peonidin 3,5-di-O-glucoside, and peonidin 3-O-glucoside, of which the predominant peonidin 3,5-di-O-glucoside represented approx. 85% of all the determined anthocyanin compounds. It was found that the petals of Rosa rugosa are a valuable source of bioactive compounds and can be considered as a healthy valuable resource.

  9. Identification of Vitis vinifera L. grape berry skin color mutants and polyphenolic profile.

    Science.gov (United States)

    Ferreira, Vanessa; Fernandes, Fátima; Pinto-Carnide, Olinda; Valentão, Patrícia; Falco, Virgílio; Martín, Juan Pedro; Ortiz, Jesús María; Arroyo-García, Rosa; Andrade, Paula B; Castro, Isaura

    2016-03-01

    A germplasm set of twenty-five grapevine accessions, forming eleven groups of possible berry skin color mutants, were genotyped with twelve microsatellite loci, being eleven of them identified as true color mutants. The polyphenolic profiling of the confirmed mutant cultivars revealed a total of twenty-four polyphenols, comprising non-colored compounds (phenolic acids, flavan-3-ols, flavonols and a stilbene) and anthocyanins. Results showed differences in the contribution of malvidin-3-O-glucoside to the characteristic Pinot Noir anthocyanins profile. Regarding the two Pique-Poul colored variants, the lighter variant was richer than the darker one in all classes of compounds, excepting anthocyanins. In Moscatel Galego Roxo the F3'H pathway seems to be more active than F3'5'H, resulting in higher amounts of cyanidin, precursor of the cyanidin derivatives. As far as we are aware, this is the first time that a relationship between the content of polyphenolic compounds is established in groups of grape berry skin color mutant cultivars. Copyright © 2015 Elsevier Ltd. All rights reserved.

  10. Comparative Fingerprint of Aromatic Herbs and Yeast Alcoholic Extracts used as Ingredients for Promen, a Prostate Preventive Nutraceutical

    Directory of Open Access Journals (Sweden)

    Florina Csernatoni

    2013-11-01

    Full Text Available The aim of this study was to characterize and identify different bioactive compounds in plant sources and yeast powders  to obtain an original nutraceutical (Promen which has beneficial effects in prostate disease prevention. Seven plant and fruit sources, namely nettle (Urtica dioica, green tea (Camellia sinensis, fluff with small flowers (Epilobium parviplorum, tomato (Solanum licopersicum,  sea buckthorn (Hippophae rhamnoides, pumpkin (Cucurbita maxima, sunflower (Helianthus annus and lyophilized beer yeast (Saccharomyces cerevisiae were investigated. Methanolic extracts were prepared using 15% plant concentration and the purified fractions were analyzed using high throughput techniques like UV-VIS spectroscopy, high performance liquid chromatography coupled with photodiode array detection (HPLC-DAD and mass spectrometry LC-QTOF -MS. The majority of the investigated plants were rich in phenolic derivatives, polyphenols (flavonoid glucosides, while yeast was rich in aminoacids, peptides and vitamins B. The major compounds identified were: Juglone, Resveratrol, Quercetin, Epigallocatechin, Gallocatechin, Biochanin A, Isorhamnetin 3-O-glucoside 7-O-rhamnoside, Quercetin 3-O-galactoside 7-O-rhamnoside, Kaempferol 3,7-O-diglucoside and p-Coumaroylquinic acid. The specific biomarkers were identified for both plant extracts used as ingredients to obtain an nutraceutical  Promen. Combined UV-Vis spectroscopy, HPLC-PDA chromatography and LC-MS spectrometry are recommended as accurate, sensible and reliable tools to investigate the plants and nutraceutical fingerprints and to predict the relation between ingredients composition and their health effects.

  11. Phenolics in Primula veris L. and P. elatior (L. Hill Raw Materials

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    Katarzyna Bączek

    2017-01-01

    Full Text Available Primula veris L. and Primula elatior (L. Hill represent medicinal plants used for the production of herbal teas and preparations with antioxidant and expectorant activity. Flowers and roots of both species possess the same biological activity. In the presented study, raw materials of wild growing P. veris and P. elatior were compared in terms of the content and composition of phenolic compounds using a fast and simple HPLC-DAD method. The study showed that flowers of both species were rich in flavonoids. However, P. veris flowers were characterized with a distinctly higher content of isorhamnetin-3-O-glucoside, astragalin, and (+-catechin, whereas P. elatior occurred to be a richer source of rutoside and isorhamnetin-3-O-rutinoside. Hyperoside was found exclusively in P. elatior flowers. Phenolic glycosides (primverin and primulaverin were identified only in the roots. Their content was about ten times higher in P. veris in comparison with P. elatior underground organs. The obtained results clearly show that both Primula species differ distinctly in terms of the content and composition of phenolic compounds. The compounds differentiating both species to the highest degree (hyperoside, in flowers, as well as primverin and primulaverin, in the roots may be useful chemical markers in the identification and evaluation of both species.

  12. Antiproliferative terpenoids from almond hulls (Prunus dulcis): identification and structure-activity relationships.

    Science.gov (United States)

    Amico, Vincenzo; Barresi, Vincenza; Condorelli, Daniele; Spatafora, Carmela; Tringali, Corrado

    2006-02-08

    Bioassay-guided fractionation of the EtOAc crude extract from Sicilian almond hulls, a waste material from Prunus dulcis crop, allowed identification of 10 constituents, isolated as pure compounds (1-5, 7, and 10) or unseparable mixtures (5 + 6 and 8 + 9). All compounds were subjected to spectroscopic analysis and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide bioassay on MCF-7 human breast cancer cells. In addition to the main components oleanolic (1), ursolic (2), and betulinic (3) acids, the 2-hydroxy analogues alphitolic (4), corosolic (5), and maslinic (6) acids, as well as the related aldehydes, namely, betulinic (7), oleanolic (8), and ursolic (9), were identified. From a more polar fraction, the beta-sitosterol 3-O-glucoside (10) was also identified. A sample of commercially available betulin (11) was also included in bioassays as further support to a structure-activity relationship study. Betulinic acid showed antiproliferative activity toward MCF-7 cells (GI50 = 0.27 microM), higher than the anticancer drug 5-fluorouracil.

  13. Stress responses in alfalfa (Medicago sativa L.)

    International Nuclear Information System (INIS)

    Kessmann, H.; Edwards, R.; Dixon, R.A.; Geno, P.W.

    1990-01-01

    The isoflavonoid conjugates medicarpin-3-O-glucoside-6 double-prime-O-malonate (MGM), afrormosin-7-O-glucoside (AG), and afrormosin-7-O-glucoside-6 double-prime-O-malonate (AGM) were isolated and characterized from cell suspension cultures of alfalfa (Medicago sativa L.), where they were the major constitutive secondary metabolites. They were also found in alfalfa roots but not in other parts of the plant. The phytoalexin medicarpin accumulated rapidly in suspension cultured cells treated with elicitor from Colletotrichum lindemuthianum, and this was subsequently accompanied by an increase in the levels of MGM. In contrast, net accumulation of afrormosin conjugates was not affected by elicitor treatment. Labeling studies with [ 14 C]phenylalanine indicated that afrormosin conjugates were the major de novo synthesized isoflavonoid products in unelicited cells. During elicitation, [ 14 C]phenylalanine was incorporated predominantly into medicarpin, although a significant proportion of the newly synthesized medicarpin was also conjugated. Treatment of 14 C-labeled, elicited cells with L-α-aminooxy-β-phenylpropionic acid, a potent inhibitor of PAL activity in vivo, resulted in the initial appearance of labeled medicarpin of very low specific activity, suggesting that the phytoalexin could be released from a preformed conjugate under these conditions. Our data draw attention to the involvement of isoflavone hydroxylases during the constitutive and elicitor-induced accumulation of isoflavonoids and their conjugates in alfalfa cell cultures

  14. Different Anthocyanin Profiles of the Skin and the Pulp of Yan73 (Muscat Hamburg × Alicante Bouschet Grape Berries

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    Chang-Qing Duan

    2010-03-01

    Full Text Available Yan73 is a “teinturier” red wine variety cultivated in China and used in winemaking to strengthen red wine color. Here, the anthocyanin profile in both the skin and pulp of this grape variety was analyzed by HPLC-MS. The results showed that 18 anthocyanins were detected in both the skin and the pulp, and pelargonidin-3-O-glucoside, an anthocyanin compound hardly detected in most other Vitis viniferaberries, was found. However, the contents of individual anthocyanins in the skin and the pulp were significantly different. Compared with the skin, the pulp exhibited much lower ratio of 3’,5’-substituted to 3’-substituted anthocyanins and much higher ratio of methoxylation of anthocyanin B-ring to non methoxylation, and with regard to the aromatic acylated and aliphatic acylated anthocyanins, both their contents in the skin are higher than in the pulp. The findings will provide some new insight for the tissue-specific expression and regulation of the genes involving in anthocyanin biosynthesis in grape berries.

  15. Formation of flavone di-O-glucosides using a glycosyltransferase from Bacillus cereus.

    Science.gov (United States)

    Ahn, Byoung Chan; Kim, Bong Gyu; Jeon, Young Min; Lee, Eun Jeong; Lim, Yoongho; Ahn, Joong-Hoon

    2009-04-01

    Microbial UDP-glycosyltransferases can convert many small lipophilic compounds into glycons using uridinediphosphate- activated sugars. The glycosylation of flavonoids affects solubility, stability, and bioavailability. The gene encoding the UDP-glycosyltransferase from Bacillus cereus, BcGT-3, was cloned by PCR and sequenced. BcGT-3 was expressed in Escherichia coli BL21 (DE3) with a glutathione S-transferase tag and purified using a glutathione Stransferase affinity column. BcGT-3 was tested for activity on several substrates including genistein, kaempferol, luteolin, naringenin, and quercetin. Flavonols were the best substrates for BcGT-3. The enzyme dominantly glycosylated the 3-hydroxyl group, but the 7-hydroxyl group was glycosylated when the 3-hydroxyl group was not available. The kaempferol reaction products were identified as kaempferol-3-O-glucoside and kaempferol- 3,7-O-diglucoside. Kaempferol was the most effective substrate tested. Based on HPLC, LC/MS, and NMR analyses of the reaction products, we conclude that BcGT-3 can be used for the synthesis of kaempferol 3,7-O-diglucose.

  16. New flavonol glycosides from the leaves of Triantha japonica and Tofieldia nuda.

    Science.gov (United States)

    Iwashina, Tsukasa; Tamura, Minoru N; Murai, Yoshinori; Kitajima, Junichi

    2013-09-01

    Two new flavonol glycosides were isolated from the leaves of Triantha japonica, together with eight known flavonols, kaempferol 3-O-sophoroside, kaempferol 3-O-sambubioside, kaempferol 3-O-glucosyl-(1 --> 2)-[glucosyl-(1 --> 6)-glucoside], quercetin 3-O-sophoroside, quercetin 3-O-sambubioside, isorhamnetin 3-O-glucoside, isorhamnetin 3-O-sophoroside and isorhamnetin 3-O-sambubioside. The new compounds were identified as kaempferol 3-O-beta-xylopyranosyl-(1 --> 2)-[beta-glucopyranosyl-(1 --> 6)-beta-glucopyranoside] (1) and isorhamnetin 3-O-beta-xylopyranosyl-(1 --> 2)-[beta-glucopyranosyl-(1 --> 6)-beta-glucopyranoside] (3) by UV, LC-MS, acid hydrolysis, and 1H and 13C NMR spectroscopy. Another two new flavonol glycosides were isolated from theleaves of Tofieldia nuda, and identified as kaempferol 3-O-beta-glucopyranosyl-(1 --> 2)-[beta-glucopyranosyl-(1 --> 6)-beta-galactopyranoside] (4) and quercetin 3-O-beta-glucopyranosyl-(1 --> 2)-[beta-glucopyranosyl-(1 --> 6)-beta-galactopyranoside] (5). Though the genera Triantha and Tofieldia were treated as Tofieldia sensu lato, they were recently divided into two genera. It was shown by this survey that their flavonoid composition were also different to each other.

  17. LC-NMR, NMR, and LC-MS identification and LC-DAD quantification of flavonoids and ellagic acid derivatives in Drosera peltata.

    Science.gov (United States)

    Braunberger, Christina; Zehl, Martin; Conrad, Jürgen; Fischer, Sonja; Adhami, Hamid-Reza; Beifuss, Uwe; Krenn, Liselotte

    2013-08-01

    The herb of Drosera peltata, commonly named the shield sundew, is used as an antitussive in phytotherapy, although the plants' composition has not been determined in detail so far. Hence, in this study, we present a validated, sensitive, reliable, and cheap narrow-bore LC-DAD method for the simultaneous quantification of flavonoids and ellagic acid derivatives in this herbal drug. In addition, the structures of 13 compounds have been elucidated by LC-MS, LC-NMR, and offline NMR experiments after isolation: herbacetin-3-O-glucoside (1), gossypitrin (2), ellagic acid (3), quercetin-7-O-glucoside (4), isoquercitrin (5), kaempferol-3-O-(6″-O-galloyl)-glucoside (6), herbacetin-7-O-glucoside (7), astragalin (8), gossypetin (9), herbacetin (10), quercetin (11), 3,3'-di-O-methyl ellagic acid (12), and kaempferol (13). Compounds 1, 2, 4, 5, 6, 7, and 10 have been identified in D. peltata for the first time, and compounds 1, 4, 6, 7, and 10 have not been detected in any Drosera species before. Copyright © 2013 Elsevier B.V. All rights reserved.

  18. Chemical constituents, radical scavenging activity and enzyme inhibitory capacity of fruits from Cotoneaster pannosus Franch.

    Science.gov (United States)

    Les, Francisco; López, Víctor; Caprioli, Giovanni; Iannarelli, Romilde; Fiorini, Dennis; Innocenti, Marzia; Bellumori, Maria; Maggi, Filippo

    2017-05-24

    Cotoneaster pannosus (Rosaceae) is a semievergreen shrub, producing globose dark red pomes, native to China and widely used as an ornamental plant all over the world. Despite its extensive cultivation, little information is available on the chemical composition and biological activities of its fruits. In this work, the analysis of the chemical composition of C. pannosus fruits, in terms of phenolic components, carotenoids and ascorbic acid by HPLC/DAD, HPLC/ESI-MS and MS/MS as well as in terms of macro- and micro-nutrients was performed. The fruits proved to be a good source of shikimic acid and caffeoylquinic acids, whereas β-carotene, pelargonidin-3-O glucoside and cyanidin-3,5-rutinoside gave an important contribution to the color of the fruit. Both the polar and apolar fruit extracts showed noteworthy radical scavenger activity and inhibitory effects against monoamine oxidase A (MAO-A), tyrosinase (TYR) and α-glucosidase, making C. pannosus red pomes a promising candidate ingredient in functional foods and dietary supplements.

  19. Online extraction-high performance liquid chromatography-diode array detector-quadrupole time-of-flight tandem mass spectrometry for rapid flavonoid profiling of Fructus aurantii immaturus.

    Science.gov (United States)

    Tong, Runna; Peng, Mijun; Tong, Chaoying; Guo, Keke; Shi, Shuyun

    2018-03-01

    Chemical profiling of natural products by high performance liquid chromatography (HPLC) was critical for understanding of their clinical bioactivities, and sample pretreatment steps have been considered as a bottleneck for analysis. Currently, concerted efforts have been made to develop sample pretreatment methods with high efficiency, low solvent and time consumptions. Here, a simple and efficient online extraction (OLE) strategy coupled with HPLC-diode array detector-quadrupole time-of-flight tandem mass spectrometry (HPLC-DAD-QTOF-MS/MS) was developed for rapid chemical profiling. For OLE strategy, guard column inserted with ground sample (2 mg) instead of sample loop was connected with manual injection valve, in which components were directly extracted and transferred to HPLC-DAD-QTOF-MS/MS system only by mobile phase without any extra time, solvent, instrument and operation. By comparison with offline heat-reflux extraction for Fructus aurantii immaturus (Zhishi), OLE strategy presented higher extraction efficiency perhaps because of the high pressure and gradient elution mode. A total of eighteen flavonoids were detected according to their retention times, UV spectra, exact mass, and fragmentation ions in MS/MS spectra, and compound 9, natsudaidain-3-O-glucoside, was discovered in Zhishi for the first time. It is concluded that the developed OLE-HPLC-DAD-QTOF-MS/MS system offers new perspectives for rapid chemical profiling of natural products. Copyright © 2018. Published by Elsevier B.V.

  20. Winery by-products: extraction optimization, phenolic composition and cytotoxic evaluation to act as a new source of scavenging of reactive oxygen species.

    Science.gov (United States)

    Melo, Priscilla Siqueira; Massarioli, Adna Prado; Denny, Carina; dos Santos, Luciana Ferracini; Franchin, Marcelo; Pereira, Giuliano Elias; Vieira, Thais Maria Ferreira de Souza; Rosalen, Pedro Luiz; de Alencar, Severino Matias

    2015-08-15

    Nearly 20 million tons of winery by-products, with many biological activities, are discarded each year in the world. The extraction of bioactive compounds from Chenin Blanc, Petit Verdot, and Syrah grape by-products, produced in the semi-arid region in Brazil, was optimized by a Central Composite Rotatable Design. The phenolic compounds profile, antioxidant capacity against synthetic free radicals (DPPH and ABTS), reactive oxygen species (ROS; peroxyl radical, superoxide radical, hypochlorous acid), cytotoxicity assay (MTT) and quantification of TNF-α production in RAW 264.7 cells were conducted. Gallic acid, syringic acid, procyanidins B1 and B2, catechin, epicatechin, epicatechin gallate, quercetin 3-β-d-glucoside, delfinidin 3-glucoside, peonidin 3-O-glucoside, and malvidin 3-glucoside were the main phenolic compounds identified. In general, rachis showed higher antioxidant capacity than pomace extract, especially for Chenin Blanc. All extracts showed low cytotoxicity against RAW 264.7 cells and Petit Verdot pomace suppressed TNF-α liberation in vitro. Therefore, these winery by-products can be considered good sources of bioactive compounds, with great potential for application in the food and pharmaceutical industries. Copyright © 2015 Elsevier Ltd. All rights reserved.

  1. Comprehensive Characterization of Extractable and Nonextractable Phenolic Compounds by High-Performance Liquid Chromatography-Electrospray Ionization-Quadrupole Time-of-Flight of a Grape/Pomegranate Pomace Dietary Supplement.

    Science.gov (United States)

    Pérez-Ramírez, Iza F; Reynoso-Camacho, Rosalía; Saura-Calixto, Fulgencio; Pérez-Jiménez, Jara

    2018-01-24

    Grape and pomegranate are rich sources of phenolic compounds, and their derived products could be used as ingredients for the development of functional foods and dietary supplements. However, the profile of nonextractable or macromolecular phenolic compounds in these samples has not been evaluated. Here, we show a comprehensive characterization of extractable and nonextractable phenolic compounds of a grape/pomegranate pomace dietary supplement using high-performance liquid chromatography-electrospray ionization-quadrupole time-of-flight (HPLC-ESI-QTOF) and matrix-assisted laser desorption/ionization (MALDI)-TOF techniques. The main extractable phenolic compounds were several anthocyanins (principally malvidin 3-O-glucoside) as well as gallotannins and gallagyl derivatives; some phenolic compounds were reported in grape or pomegranate for the first time. Additionally, there was a high proportion of nonextractable phenolic compounds, including vanillic acid, and dihydroxybenzoic acid. Unidentified polymeric structures were detected by MALDI-TOF MS analysis. This study shows that mixed grape and pomegranate pomaces are a source of different classes of phenolic compounds including a high proportion of nonextractable phenolic compounds.

  2. Mulberry Fruit Extract Affords Protection against Ethyl Carbamate-Induced Cytotoxicity and Oxidative Stress

    Directory of Open Access Journals (Sweden)

    Wei Chen

    2017-01-01

    Full Text Available Ethyl carbamate (EC is a food and environmental toxicant and is a cause of concern for human exposure. Several studies indicated that EC-induced toxicity was associated with oxidative stress. Mulberry fruits are reported to have a wide range of bioactive compounds and pharmacological activities. The present study was therefore aimed to investigate the protective property of mulberry fruit extract (MFE on EC-induced cytotoxicity and oxidative stress. Chemical composition analysis showed that total phenolic content and total flavonoid content in MFE were 502.43 ± 5.10 and 219.12 ± 4.45 mg QE/100 g FW. Cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside were the major anthocyanins in MFE. In vitro antioxidant studies (DPPH, ABTS, and FRAP assays jointly exhibited the potent antioxidant capacity of MFE. Further study indicated that MFE protected human liver HepG2 cells from EC-induced cytotoxicity by scavenging overproduced cellular ROS. EC treatment promoted intracellular glutathione (GSH depletion and caused mitochondrial membrane potential (MMP collapse, as well as mitochondrial membrane lipid peroxidation, whereas MFE pretreatment significantly inhibited GSH depletion and restored the mitochondrial membrane function. Overall, our study suggested that polyphenolic-rich MFE could afford a potent protection against EC-induced cytotoxicity and oxidative stress.

  3. Metabolomic profiling and sensorial quality of 'Golden Delicious', 'Liberty', 'Santana', and 'Topaz' apples grown using organic and integrated production systems.

    Science.gov (United States)

    Vanzo, Andreja; Jenko, Mojca; Vrhovsek, Urska; Stopar, Matej

    2013-07-03

    Apple quality was investigated in the scab-resistant 'Liberty', 'Santana', and 'Topaz' cultivars and the scab-susceptible 'Golden Delicious' cultivar. Trees subjected to the same crop load were cultivated using either an organic (ORG) or an integrated production (IP) system. Physicochemical properties, phenolic content, and sensorial quality of fruit from both systems were compared. There were no significant differences in fruit mass, starch, and total soluble solid content (the latter was higher in ORG 'Liberty') between ORG and IP fruit, whereas significantly higher flesh firmness was found in ORG fruit (except no difference in 'Golden Delicious'). Significantly higher total phenolic content in ORG fruit was found in 'Golden Delicious', whereas differences in other cultivars were not significant. Targeted metabolomic profiling of multiple classes of phenolics confirmed the impact of the production system on the 'Golden Delicious' phenolic profile as higher levels of 4-hydroxybenzoic acid, neo- and chlorogenic acids, phloridzin, procyanidin B2+B4, -3-O-glucoside and -3-O-galactoside of quercetin, kaempferol-3-O-rutinoside, and rutin being found in ORG fruit. The results obtained suggested that scab resistance influenced the phenolic biosynthesis in relation to the agricultural system. Sensorial evaluation indicated significantly better flavor (except for 'Topaz') and better appearance of IP fruit.

  4. Evaluation of ozonation technique for pesticide residue removal and its effect on ascorbic acid, cyanidin-3-glucoside, and polyphenols in apple (Malus domesticus) fruits.

    Science.gov (United States)

    Swami, Saurabh; Muzammil, Raunaq; Saha, Supradip; Shabeer, Ahammed; Oulkar, Dasharath; Banerjee, Kaushik; Singh, Shashi Bala

    2016-05-01

    Ozonated water dip technique was evaluated for the detoxification of six pesticides, i.e., chlorpyrifos, cypermethrin, azoxystrobin, hexaconazole, methyl parathion, and chlorothalonil from apple fruits. Results revealed that ozonation was better than washing alone. Ozonation for 15 min decreased residues of the test pesticides in the range of from 26.91 to 73.58%, while ozonation for 30 min could remove the pesticide residues by 39.39-95.14 % compared to 19.05-72.80 % by washing. Cypermethrin was the least removed pesticide by washing as well as by ozonation. Chlorothalonil, chlorpyrifos, and azoxystrobin were removed up to 71.45-95.14 % in a 30-min ozonation period. In case of methyl parathion removal, no extra advantage could be obtained by ozonation. The HPLC analysis indicated that ozonation also affected adversely the ascorbic acid and cyanidin-3-glucoside content of apples. However, 11 polyphenols studied showed a mixed trend. Gallic acid, 3,4-dihydroxybenzoic acid, catechin, epicatechin, p-coumaric acid, quercetin-3-O-glucoside, quercetin, and kaempferol were found to decrease while syringic acid, rutin, and resveratrol were found to increase in 30-min ozonation.

  5. Protective property of mulberry digest against oxidative stress - A potential approach to ameliorate dietary acrylamide-induced cytotoxicity.

    Science.gov (United States)

    Zhang, Linxia; Xu, Yang; Li, Yuting; Bao, Tao; Gowd, Vemana; Chen, Wei

    2017-09-01

    The aim of this study was investigating the protective effect of mulberry digest (MBD) on acrylamide-induced oxidative stress. Composition analysis of MBD revealed that it contained six major phenolic compounds (quercetin-3-O-rutinoside, quercetin hexoside, quercetin rhamnosylhexoside hexoside, kaempferol rhamnosylhexoside, cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside). After in vitro digestion, the contents of two anthocyanins were both decreased significantly, while the contents of four flavonoid glycosides were all increased. In addition, MBD was found to successfully suppress acrylamide-induced ROS overproduction, restore the mitochondrial membrane potential, and inhibit the mitochondrial membrane lipid peroxidation and glutathione depletion. More interestingly, the protective effect of MBD against acrylamide-induced oxidative damage was enhanced compared with mulberry fruits without digestion (MBE). Further study revealed that MBD enhanced the cell resistance capacity to acrylamide-induced oxidative stress, rather than its direct reaction with acrylamide. Overall, our results indicate that MBD provides a potent protection against acrylamide-induced oxidative stress. Copyright © 2017 Elsevier Ltd. All rights reserved.

  6. Carotenoids, Phenolic Profile, Mineral Content and Antioxidant Properties in Flesh and Peel of Prunus persica Fruits during Two Maturation Stages.

    Science.gov (United States)

    Dabbou, Samia; Maatallah, Samira; Castagna, Antonella; Guizani, Monia; Sghaeir, Wala; Hajlaoui, Hichem; Ranieri, Annamaria

    2017-03-01

    Carotenoids and phenolic profile, antioxidant activity as well as concentrations of selected macronutrients (K, N, Mg, Ca and Na) and micronutrients (Zn, Cu and Mn) in flesh and peel of peach fruit were recorded at two harvest dates. Predominant mineral was potassium, followed by calcium, magnesium and sodium. The concentration of most micronutrients was greater in the peel than in the flesh especially in early season. The concentration of most elements in flesh and peel decreased during fruit maturation. Total carotenoids content varied with respect to the cultivar. β-cryptoxanthin and β-carotene were the major carotenoids in both tissues and flesh contain the lowest amounts. Neochlorogenic acid, chlorogenic acid, catechin, epicatechin, gallic acid, rutin, quercetin-3-O-galactoside, cyanidin-3-O-glucoside, cyanidin-3-O-rutinoside, were detected in both peel and flesh, with chlorogenic acid and catechin being the predominant components. Peel extracts showed markedly higher antioxidant activities, when estimated by ABTS or DPPH assays, than the flesh counterparts, consistent with the observed higher phenolic content. Overall, total phenolics levels increased at full ripening stage in both peel and flesh. The results found herein provide important data on carotenoids, phenolic and macro- and micronutrient changes during fruit growth, and emphases peach fruit as a potential functional food.

  7. Effect of ultrasound irradiation on the evolution of color properties and major phenolic compounds in wine during storage.

    Science.gov (United States)

    Zhang, Qing-An; Wang, Ting-Ting

    2017-11-01

    In this paper, the effects of ultrasound irradiation were investigated on the evolution of color properties and major phenolic compounds during wine storage. The results indicate that the changing trends of color parameters are very similar in both the ultrasonically-treated and untreated wines, meanwhile the evolutions of malvidin-3-O-glucoside, monomeric flavan-3-ols and phenolic acids also demonstrate some similar patterns in all wines during storage, respectively. In summary, the ultrasound irradiation does not only temporally influence the color characteristics and phenolic compounds of wine, but also have a longer effect on their evolutions during wine storage. Furthermore, the ultrasonically-treated wine had a quicker changing trend than that of the untreated wine regarding the studied parameters. All these results indicate that the ultrasound might be as a feasible and promising novel technology for wineries to produce more red wines with the similar quality as the traditionally-aged wine in a shorter time. Copyright © 2017 Elsevier Ltd. All rights reserved.

  8. A fluorescence quenching test for the detection of flavonoid transformation.

    Science.gov (United States)

    Schoefer, L; Braune, A; Blaut, M

    2001-11-13

    A novel fluorescence quenching test for the detection of flavonoid degradation by microorganisms was developed. The test is based on the ability of the flavonoids to quench the fluorescence of 1,6-diphenyl-1,3,5-hexatriene (DPH). Several members of the anthocyanidins, flavones, isoflavones, flavonols, flavanones, dihydroflavanones, chalcones, dihydrochalcones and catechins were tested with regard to their quenching properties. The anthocyanidins were the most potent quenchers of DPH fluorescence, while the flavanones, dihydroflavanones and dihydrochalcones, quenched the fluorescence only weakly. The catechins had no visible impact on DPH fluorescence. The developed test allows a quick and easy differentiation between flavonoid-degrading and flavonoid-non-degrading bacteria. The investigation of individual reactions of flavonoid transformation with the developed test system is also possible.

  9. Extraction And Stability Of Natural Colorant From Red Glutinous Rice Bran (Oryza Sativa Glutinosa

    Directory of Open Access Journals (Sweden)

    Tirza Hanum

    2001-04-01

    Full Text Available Three extraction methods were studied to isolate natural colorant from red glutinous rice bran. Stability of extracts in relation to processing conditions and in the model beverages was determined at room temperature. Identifications of anthocyanidins was performed using reversed phase HPLC. Extraction method using acidified methanol solvent showed the highest yield (260,24+28,64 mg/100g. HPLC patern indicated the presence of six major anthocyanidins, two of them were identified as apigenidin and apigenin. Stability of anthocyanin colorant was higher in a lower acid condition and was reduced to the lowest value of 49,4, 65,4, 40,8 and 36,6% by high temperature, UV light, sunlight, and the presence of oxidator agent. respectively. Retention of antocyanin in tanin and ascorbic acid added into the model beverages was lower than in protein containing beverage or control.

  10. The Arabidopsis UDP-glycosyltransferases UGT79B2 and UGT79B3, contribute to cold, salt and drought stress tolerance via modulating anthocyanin accumulation.

    Science.gov (United States)

    Li, Pan; Li, Yan-Jie; Zhang, Feng-Ju; Zhang, Gui-Zhi; Jiang, Xiao-Yi; Yu, Hui-Min; Hou, Bing-Kai

    2017-01-01

    The plant family 1 UDP-glycosyltransferases (UGTs) are the biggest GT family in plants, which are responsible for transferring sugar moieties onto a variety of small molecules, and control many metabolic processes; however, their physiological significance in planta is largely unknown. Here, we revealed that two Arabidopsis glycosyltransferase genes, UGT79B2 and UGT79B3, could be strongly induced by various abiotic stresses, including cold, salt and drought stresses. Overexpression of UGT79B2/B3 significantly enhanced plant tolerance to low temperatures as well as drought and salt stresses, whereas the ugt79b2/b3 double mutants generated by RNAi (RNA interference) and CRISPR-Cas9 strategies were more susceptible to adverse conditions. Interestingly, the expression of UGT79B2 and UGT79B3 is directly controlled by CBF1 (CRT/DRE-binding factor 1, also named DREB1B) in response to low temperatures. Furthermore, we identified the enzyme activities of UGT79B2/B3 in adding UDP-rhamnose to cyanidin and cyanidin 3-O-glucoside. Ectopic expression of UGT79B2/B3 significantly increased the anthocyanin accumulation, and enhanced the antioxidant activity in coping with abiotic stresses, whereas the ugt79b2/b3 double mutants showed reduced anthocyanin levels. When overexpressing UGT79B2/B3 in tt18 (transparent testa 18), a mutant that cannot synthesize anthocyanins, both genes fail to improve plant adaptation to stress. Taken together, we demonstrate that UGT79B2 and UGT79B3, identified as anthocyanin rhamnosyltransferases, are regulated by CBF1 and confer abiotic stress tolerance via modulating anthocyanin accumulation. © 2016 The Authors The Plant Journal © 2016 John Wiley & Sons Ltd.

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

    Science.gov (United States)

    Wang, Hongxia; Fan, Weijuan; Li, Hong; Yang, Jun; Huang, Jirong; Zhang, Peng

    2013-01-01

    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.

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

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    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.

  13. Antimicrobial Air Filters Using Natural Euscaphis japonica Nanoparticles.

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    Gi Byoung Hwang

    Full Text Available Controlling bioaerosols has become more important with increasing participation in indoor activities. Treatments using natural-product nanomaterials are a promising technique because of their relatively low toxicity compared to inorganic nanomaterials such as silver nanoparticles or carbon nanotubes. In this study, antimicrobial filters were fabricated from natural Euscaphis japonica nanoparticles, which were produced by nebulizing E. japonica extract. The coated filters were assessed in terms of pressure drop, antimicrobial activity, filtration efficiency, major chemical components, and cytotoxicity. Pressure drop and antimicrobial activity increased as a function of nanoparticle deposition time (590, 855, and 1150 µg/cm2(filter at 3-, 6-, and 9-min depositions, respectively. In filter tests, the antimicrobial efficacy was greater against Staphylococcus epidermidis than Micrococcus luteus; ~61, ~73, and ~82% of M. luteus cells were inactivated on filters that had been coated for 3, 6, and 9 min, respectively, while the corresponding values were ~78, ~88, and ~94% with S. epidermidis. Although statistically significant differences in filtration performance were not observed between samples as a function of deposition time, the average filtration efficacy was slightly higher for S. epidermidis aerosols (~97% than for M. luteus aerosols (~95%. High-performance liquid chromatography (HPLC and electrospray ionization-tandem mass spectrometry (ESI/MS analyses confirmed that the major chemical compounds in the E. japonica extract were 1(ß-O-galloyl pedunculagin, quercetin-3-O-glucuronide, and kaempferol-3-O-glucoside. In vitro cytotoxicity and disk diffusion tests showed that E. japonica nanoparticles were less toxic and exhibited stronger antimicrobial activity toward some bacterial strains than a reference soluble nickel compound, which is classified as a human carcinogen. This study provides valuable information for the development of a

  14. Botanical Polyphenols Mitigate Microglial Activation and Microglia-Induced Neurotoxicity: Role of Cytosolic Phospholipase A2.

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    Chuang, Dennis Y; Simonyi, Agnes; Cui, Jiankun; Lubahn, Dennis B; Gu, Zezong; Sun, Grace Y

    2016-09-01

    Microglia play a significant role in the generation and propagation of oxidative/nitrosative stress, and are the basis of neuroinflammatory responses in the central nervous system. Upon stimulation by endotoxins such as lipopolysaccharides (LPS), these cells release pro-inflammatory factors which can exert harmful effects on surrounding neurons, leading to secondary neuronal damage and cell death. Our previous studies demonstrated the effects of botanical polyphenols to mitigate inflammatory responses induced by LPS, and highlighted an important role for cytosolic phospholipase A2 (cPLA2) upstream of the pro-inflammatory pathways (Chuang et al. in J Neuroinflammation 12(1):199, 2015. doi: 10.1186/s12974-015-0419-0 ). In this study, we investigate the action of botanical compounds and assess whether suppression of cPLA2 in microglia is involved in the neurotoxic effects on neurons. Differentiated SH-SY5Y neuroblastoma cells were used to test the neurotoxicity of conditioned medium from stimulated microglial cells, and WST-1 assay was used to assess for the cell viability of SH-SY5Y cells. Botanicals such as quercetin and honokiol (but not cyanidin-3-O-glucoside, 3CG) were effective in inhibiting LPS-induced nitric oxide (NO) production and phosphorylation of cPLA2. Conditioned medium from BV-2 cells stimulated with LPS or IFNγ caused neurotoxicity to SH-SY5Y cells. Decrease in cell viability could be ameliorated by pharmacological inhibitors for cPLA2 as well as by down-regulating cPLA2 with siRNA. Botanicals effective in inhibition of LPS-induced NO and cPLA2 phosphorylation were also effective in ameliorating microglial-induced neurotoxicity. Results demonstrated cytotoxic factors from activated microglial cells to cause damaging effects to neurons and potential use of botanical polyphenols to ameliorate the neurotoxic effects.

  15. The effect of dietary factors on strawberry anthocyanins oral bioavailability.

    Science.gov (United States)

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

    2017-11-15

    Strawberries are a dietary source of anthocyanins, particularly pelargonidin glycosides. Dietary anthocyanins have received increasing attention among researchers and consumers due to their health benefits. The oral bioavailability of anthocyanins is reported to be low and various dietary factors may influence their oral bioavailability further. Milk is suggested to reduce (poly)phenols' oral bioavailability. However, the effect of milk on anthocyanin oral bioavailability remains uncertain. Likewise, mixed nutrient meals may influence the oral bioavailability of anthocyanins. Therefore, the purpose of this study was to assess the effect of milk on the oral bioavailability and other pharmacokinetic (PK) variables of strawberry anthocyanins consumed with and without a meal. Nine healthy participants consumed a strawberry beverage prepared in milk or water with a standard meal on two occasions. On two additional occasions, the beverages were given to a subset (n = 4) of participants to determine the impact of the meal on anthocyanin PK variables, including oral bioavailability. Independent of the meal, beverages prepared in milk significantly reduced the peak plasma concentrations (C max ) of pelargonidin-3-O-glucoside (P-3-G), pelargonidin-glucuronide (PG) and pelargonidin-3-O-rutinoside (P-3-R), as well as the PG and P-3-R area under the curve (AUC) (p bioavailability of pelargonidin anthocyanins under meal conditions; however, the oral relative bioavailability of pelargonidin anthocyanins was reduced by ∼50% by milk under without meal conditions (p < 0.05). Consuming strawberry beverages made with milk and consuming those made with water with and without a meal influenced different aspects of strawberry anthocyanin PKs. The significance of this effect on clinical efficacy requires additional research.

  16. Characterisation of phenolic compounds in wild fruits from Northeastern Portugal.

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    Guimarães, Rafaela; Barros, Lillian; Dueñas, Montserrat; Carvalho, Ana Maria; Queiroz, Maria João R P; Santos-Buelga, Celestino; Ferreira, Isabel C F R

    2013-12-15

    This study aimed to analyse the phenolic composition of wild fruits of Arbutus unedo (strawberry-tree), Prunus spinosa (blackthorn), Rosa canina and Rosa micrantha (wild roses). Analyses were performed by HPLC-DAD-ESI/MS. P spinosa fruits presented the highest concentration in phenolic acids (29.78 mg/100 g dry weight), being 3-O-caffeoylquinic acid the most abundant one, and flavone/ols (57.48 mg/100 g), among which quercetin3-O-rutinoside (15.63 mg/100 g) was the majority compound. (+)-Catechin was the most abundant compound in A. unedo (13.51 mg/100 g) and R. canina (3.59 mg/100 g) fruits. A. unedo fruits presented the highest concentration in flavan-3-ols (36.30 mg/100 g). Cyanidin 3-O-glucoside was found in all the studied fruits, being the major anthocyanin in most of them, with the exception of P. spinosa samples, in which cyaniding 3-O-rutinoside and peonidin 3-O-rutinoside predominated; P. spinosa fruit presented the more complex anthocyanin profile among the analysed fruits and also the highest anthocyanin concentrations, which was coherent with its greater pigmentation. All in all, P. spinosa presented the highest levels of phenolic acids and flavonoids, including anthocyanins, flavonols and flavones, although no flavan-3-ols could be identified in its fruits. The present study represents a contribution to the chemical characterisation of phenolic compounds from wild fruits with acknowledged antioxidant activity and traditionally used for several folk medicinal applications. Copyright © 2013 Elsevier Ltd. All rights reserved.

  17. Deciphering the interplay among genotype, maturity stage and low-temperature storage on phytochemical composition and transcript levels of enzymatic antioxidants in Prunus persica fruit.

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    Manganaris, George A; Drogoudi, Pavlina; Goulas, Vlasios; Tanou, Georgia; Georgiadou, Egli C; Pantelidis, George E; Paschalidis, Konstantinos A; Fotopoulos, Vasileios; Manganaris, Athanasios

    2017-10-01

    The aim of this study was to understand the antioxidant metabolic changes of peach (cvs. 'Royal Glory', 'Red Haven' and 'Sun Cloud') and nectarine fruits (cv. 'Big Top') exposed to different combinations of low-temperature storage (0, 2, 4 weeks storage at 0 °C, 90% R.H.) and additional ripening at room temperature (1, 3 and 5 d, shelf life, 20 °C) with an array of analytical, biochemical and molecular approaches. Initially, harvested fruit of the examined cultivars were segregated non-destructively at advanced and less pronounced maturity stages and qualitative traits, physiological parameters, phytochemical composition and antioxidant capacity were determined. 'Big Top' and 'Royal Glory' fruits were characterized by slower softening rate and less pronounced ripening-related alterations. The coupling of HPLC fingerprints, consisted of 7 phenolic compounds (chlorogenic, neochlorogenic acid, catechin, epicatechin, rutin, quecetin-3-O-glucoside, procyanidin B1) and spectrophotometric methods disclosed a great impact of genotype on peach bioactive composition, with 'Sun Cloud' generally displaying the highest contents. Maturity stage at harvest did not seem to affect fruit phenolic composition and no general guidelines for the impact of cold storage and shelf-life on individual phenolic compounds can be extrapolated. Subsequently, fruit of less pronounced maturity at harvest were used for further molecular analysis. 'Sun Cloud' was proven efficient in protecting plasmid pBR322 DNA against ROO attack throughout the experimental period and against HO attack after 2 and 4 weeks of cold storage. Interestingly, a general down-regulation of key genes implicated in the antioxidant apparatus with the prolongation of storage period was recorded; this was more evident for CAT, cAPX, Cu/ZnSOD2, perAPX3 and GPX8 genes. Higher antioxidant capacity of 'Sun Cloud' fruit could potentially be linked with compounds other than enzymatic antioxidants that further regulate peach

  18. UPLC-QTOF-MS metabolomics analysis revealed the contributions of metabolites to the pathogenesis of Rhizoctonia solani strain AG-1-IA.

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    Wenjin Hu

    Full Text Available To explore the pathogenesis of Rhizoctonia solani and its phytotoxin phenylacetic acid (PAA on maize leaves and sheaths, treated leaf and sheath tissues were analyzed and interpreted by ultra-performance liquid chromatography-mass spectrometry combined with chemometrics. The PAA treatment had similar effects to those of R. solani on maize leaves regarding the metabolism of traumatin, phytosphingosine, vitexin 2'' O-beta-D-glucoside, rutin and DIBOA-glucoside, which were up-regulated, while the synthesis of OPC-8:0 and 12-OPDA, precursors for the synthesis of jasmonic acid, a plant defense signaling molecule, was down-regulated under both treatments. However, there were also discrepancies in the influences exhibited by R. solani and PAA as the metabolic concentration of zeaxanthin diglucoside in the R. solani infected leaf group decreased. Conversely, in the PAA-treated leaf group, the synthesis of zeaxanthin diglucoside was enhanced. Moreover, although the synthesis of 12 metabolites were suppressed in both the R. solani- and PAA-treated leaf tissues, the inhibitory effect of R. solani was stronger than that of PAA. An increased expression of quercitrin and quercetin 3-O-glucoside was observed in maize sheaths treated by R. solani, while their concentrations were not changed significantly in the PAA-treated sheaths. Furthermore, a significant decrease in the concentration of L-Glutamate, which plays important roles in plant resistance to necrotrophic pathogens, only occurred in the R. solani-treated sheath tissues. The differentiated metabolite levels may be the partial reason of why maize sheaths were more susceptible to R. solani than leaves and may explain the underlying mechanisms of R. solani pathogenesis.

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

    Science.gov (United States)

    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 products.

  20. Analysis of Phenolic Acids of Jerusalem Artichoke (Helianthus tuberosus L. Responding to Salt-Stress by Liquid Chromatography/Tandem Mass Spectrometry

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    Fujia Chen

    2014-01-01

    Full Text Available Plant phenolics can have applications in pharmaceutical and other industries. To identify and quantify the phenolic compounds in Helianthus tuberosus leaves, qualitative analysis was performed by a reversed phase high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS and quantitative analysis by HPLC. Ten chlorogenic acids (CGAs were identified (3-o-caffeoylquinic acid, two isomers of caffeoylquinic acid, caffeic acid, p-coumaroyl-quinic acid, feruloylquinic acid, 3,4-dicaffeoyquinic acid, 3,5-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid by comparing their retention times, UV-Vis absorption spectra, and MS/MS spectra with standards. In addition, four other phenolic compounds, including caffeoyl glucopyranose, isorhamnetin glucoside, kaempferol glucuronide, and kaempferol-3-o-glucoside, were tentatively identified in Helianthus tuberosus leaves for the first time. The 3-o-caffeoylquinic acid (7.752 mg/g DW, 4,5-dicaffeoylquinic acid (5.633 mg/g DW, and 3,5-dicaffeoylquinic acid (4.900 mg/g DW were the major phenolic compounds in leaves of Helianthus tuberosus cultivar NanYu in maturity. The variations in phenolic concentrations and proportions in Helianthus tuberosus leaves were influenced by genotype and plant growth stage. Cultivar NanYu had the highest concentration of phenolic compounds, in particular 3-o-caffeoylquinic acid and 4,5-dicaffeoylquinic acid compared with the other genotypes (wild accession and QingYu. Considering various growth stages, the concentration of total phenolics in cultivar NanYu was higher at flowering stage (5.270 mg/g DW than at budding and tuber swelling stages. Cultivar NanYu of Helianthus tuberosus is a potential source of natural phenolics that may play an important role in the development of pharmaceuticals.

  1. Insights on the chemical basis of the astringency of Spanish red wines.

    Science.gov (United States)

    Sáenz-Navajas, María-Pilar; Avizcuri, José-Miguel; Ferreira, Vicente; Fernández-Zurbano, Purificación

    2012-10-01

    The main goal of the present study is to provide an insight on the role played by non-volatile molecules on the different in-mouth attributes, particularly astringency. For achieving such goal, the main in-mouth sensory attributes of 34 oaked Spanish red wines were measured by a trained panel. The wine content in 30 sensory-active molecules was analysed by different HPLC based methodologies together with classical enological parameters and two proanthocyanidin indexes. Fourteen compounds (aconitic acids, polymeric proanthocyanidins, caftaric, caffeic and coutaric acids and seven quercetins) were found to be at concentrations above reported taste thresholds and to have a reasonably high range of occurrence. Two highly statistically significant models for astringency were built with those compounds. Even if the models could not be fully validated by sensory addition experiments, the research has demonstrated that wine astringency is driven by polymeric proanthocyanidins and by certain phenolic acids, the rate trans/cis-aconitic acid and flavonol profiles. The research has highlighted the existence of extremely complex interactions between non-volatile compounds on the in-mouth sensory perception. Particularly remarkable is the lack of additivity and potential antagonism found between the pairs cis/trans-aconitic acids, between aconitic and caffeic acids and between quercetin-3-O-galactoside and quercetin-3-O-glucoside. Also remarkable was the sweetness×astringent interaction and the matrix-dependence of the sensory responses elicited by flavonols. These results suggest the need for new paradigms and experimental procedures for fully decoding the real sensory relevance of individual non-volatile compounds in the overall wine flavour. Copyright © 2012 Elsevier Ltd. All rights reserved.

  2. Effect of terroir on the phenolic compounds of Muscat of Bornova Wines from 3 different sub-regions of Aegean, Turkey

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    Karaoğlan Selin N. Yabaci

    2015-01-01

    Full Text Available Characterization of the phenolic compounds of wines from Muscat of Bornova, a native aromatic white grape variety (Vitis vinifera grown in the Aegean region of Turkey and the influence of terroir (Menderes, Halilbeyli and Kemaliye sub- regions on these compounds were investigated. From Muscat of Bornova growing sub regions, Menderes/İzmir has a typical Mediterranean climate at around 90 m altitude which is located Eagean cost area with a fertile sandy-loamy soil; Halilbeyli/İzmir sub-region is located in inner İzmir, close to Manisa with 115 m altitude with same soil structure of Menderes. Kemaliye/Manisa has a transition climate between Mediterranean and continental climate at about 245 m altitude. Its soil is pale with a distinct amount of lime (∼30% and sandy-loamy, as well. High performance liquid chromatography-diode array dedector (HPLC-DAD and mass spectrometry (MS were used for the phenolic compounds analysis. Four flavanols, eight phenolic acids and a flavonol were identified and quantified. It was observed that the total phenolic content in the Halilbeyli sub-region was the highest, fol- lowed by the Menderes and Kemaliye sub-regions. Procyanidin B4 was the most abundant flavanol and quercetin-3-O-glucoside was the only flavonol identified in all regions’ wines. Sensory analysis was also used to investigate the influences of terroir. Statistically significant (0.05 regional differences were observed. Based upon sensory analysis, the wine obtained from Halilbeyli was darker in color, and had more astringency and bitterness than the others, and was the least popular wine. Kemaliye and Menderes were both preferred due to their better coloring, flavour, less astringency and bitterness attributes.

  3. Integrated metabolo-proteomic approach to decipher the mechanisms by which wheat QTL (Fhb1 contributes to resistance against Fusarium graminearum.

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    Raghavendra Gunnaiah

    Full Text Available BACKGROUND: Resistance in plants to pathogen attack can be qualitative or quantitative. For the latter, hundreds of quantitative trait loci (QTLs have been identified, but the mechanisms of resistance are largely unknown. Integrated non-target metabolomics and proteomics, using high resolution hybrid mass spectrometry, were applied to identify the mechanisms of resistance governed by the fusarium head blight resistance locus, Fhb1, in the near isogenic lines derived from wheat genotype Nyubai. FINDINGS: The metabolomic and proteomic profiles were compared between the near isogenic lines (NIL with resistant and susceptible alleles of Fhb1 upon F. graminearum or mock-inoculation. The resistance-related metabolites and proteins identified were mapped to metabolic pathways. Metabolites of the shunt phenylpropanoid pathway such as hydroxycinnamic acid amides, phenolic glucosides and flavonoids were induced only in the resistant NIL, or induced at higher abundances in resistant than in susceptible NIL, following pathogen inoculation. The identities of these metabolites were confirmed, with fragmentation patterns, using the high resolution LC-LTQ-Orbitrap. Concurrently, the enzymes of phenylpropanoid biosynthesis such as cinnamyl alcohol dehydrogenase, caffeoyl-CoA O-methyltransferase, caffeic acid O-methyltransferase, flavonoid O-methyltransferase, agmatine coumaroyltransferase and peroxidase were also up-regulated. Increased cell wall thickening due to deposition of hydroxycinnamic acid amides and flavonoids was confirmed by histo-chemical localization of the metabolites using confocal microscopy. CONCLUSION: The present study demonstrates that the resistance in Fhb1 derived from the wheat genotype Nyubai is mainly associated with cell wall thickening due to deposition of hydroxycinnamic acid amides, phenolic glucosides and flavonoids, but not with the conversion of deoxynivalenol to less toxic deoxynivalenol 3-O-glucoside.

  4. Simultaneous determination of phenolic compounds in Cynthiana grape (Vitis aestivalis) by high performance liquid chromatography-electrospray ionisation-mass spectrometry.

    Science.gov (United States)

    Ramirez-Lopez, L M; McGlynn, W; Goad, C L; Mireles Dewitt, C A

    2014-04-15

    Phenolic acids, flavanols, flavonols and stilbenes (PAFFS) were isolated from whole grapes, juice, or pomace and purified using enzymatic hydrolysis. Only anthocyanin mono-glucosides and a few of the oligomers from Cynthiana grape (Vitis aestivalis) were analysed. Flavonoid-anthocyanin mono-glucosides (FA) were isolated using methanol/0.1% hydrochloric acid extraction. In addition, crude extractions of phenolic compounds from Cynthiana grape using 50% methanol, 70% methanol, 50% acetone, 0.01% pectinase, or petroleum ether were also evaluated. Reverse phase high performance liquid chromatography (RP-HPLC) with photodiode array (PDA) detector was used to identify phenolic compounds. A method was developed for simultaneous separation, identification and quantification of both PAFFS and FA. Quantification was performed by the internal standard method using a five points regression graph of the UV-visible absorption data collected at the wavelength of maximum absorbance for each analyte. From whole grape samples nine phenolic compounds were tentatively identified and quantified. The individual phenolic compounds content varied from 3 to 875 mg kg⁻¹ dry weight. For juice, twelve phenolic compounds were identified and quantified. The content varied from 0.07 to 910 mg kg⁻¹ dry weight. For pomace, a total of fifteen phenolic compounds were tentatively identified and quantified. The content varied from 2 mg kg⁻¹ to 198 mg kg⁻¹ dry matter. Results from HPLC analysis of the samples showed that gallic acid and (+)-catechin hydrate were the major phenolic compounds in both whole grapes and pomace. Cyanidin and petunidin 3-O-glucoside were the major anthocyanin glucosides in the juice. Published by Elsevier Ltd.

  5. Unravelling the bioherbicide potential of Eucalyptus globulus Labill: Biochemistry and effects of its aqueous extract.

    Science.gov (United States)

    Puig, Carolina G; Reigosa, Manuel J; Valentão, Patrícia; Andrade, Paula B; Pedrol, Nuria

    2018-01-01

    In the worldwide search for new strategies in sustainable weed management, the use of plant species able to produce and release phytotoxic compounds into the environment could be an effective alternative to synthetic herbicides. Eucalyptus globulus Labill. is known to be a source of biologically active compounds responsible for its phytotoxic and allelopathic properties. Our previous results demonstrated the bioherbicide potential of eucalyptus leaves incorporated into the soil as a green manure, probably through the release of phytotoxins into the soil solution. Thus, the aims of this study were to understand the phytotoxicity of the eucalyptus leaves aqueous extract applied in pre- and post-emergence, and to identify and quantify its potentially phytotoxic water-soluble compounds. The effects were tested on the germination and early growth of the model target species Lactuca sativa and Agrostis stolonifera, and on physiological parameters of L. sativa adult plants after watering or spraying application. Dose-response curves and ED50 and ED80 values for eucalyptus aqueous extracts revealed pre-emergence inhibitory effects on both target species, effects being comparable to the herbicide metolachlor. While spraying treatment reduced the aerial and root biomass and increased the dry weight/fresh weight ratio of lettuce adult plants, watering application reduced protein contents and chlorophyll concentrations with respect to control, reflecting different modes of action depending on the site of phytotoxin entry. Via HPLC analyses, a total of 8 phenolic compounds (chlorogenic, two ρ-coumaric derivatives, ellagic, hyperoside, rutin, quercitrin, and kaempferol 3-O-glucoside) and other 5 low weight organic acids (citric, malic, shikimic, succinic and fumaric acids) were obtained from aqueous extract, the latter being identified for the first time in E. globulus. Despite some phytotoxic effects were found on lettuce adult plants, the use of eucalyptus aqueous extract

  6. Box-Behnken factorial design to obtain a phenolic-rich extract from the aerial parts of Chelidonium majus L.

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    Grosso, Clara; Ferreres, Federico; Gil-Izquierdo, Angel; Valentão, Patrícia; Sampaio, Maria; Lima, Júlio; Andrade, Paula B

    2014-12-01

    A Box-Behnken design (BBD) was developed to study the influence of four parameters (X1: % methanol; X2: extraction time; X3: extraction temperature; X4: solid/solvent ratio) on two responses, namely extraction yield and phenolics content of the aerial parts of Chelidonium majus L. The model presented a good fit to the experimental results for the extraction yield, being significantly influenced by X1 and X4. On the other hand a parameter reduction was necessary to run the model for phenolics content, showing that only X1 and X2 had great influence on the response. Two best extraction conditions were defined: X1=76.8% MeOH, X2=150.0 min, X3=60.0°C and X4=1:100 and X1=69.2%, X2=150 min, X3=42.5°C and X4=1:100. Moreover, the HPLC-DAD-ESI/MS(n) analysis conducted with the center point sample revealed the presence of 15 alkaloids and 15 phenolic compounds, from which the 9 flavonoids and 3 hydroxycinnamic acids are described for the first time. Only phenolic compounds were quantified by a validated HPLC-DAD method, the pair quercetin-3-O-rutinoside+quercetin-3-O-glucoside dominating all the 29 extracts. This study is of great importance for future works that seek to apply the phenolic profile to the quality control of C. majus samples. Copyright © 2014 Elsevier B.V. All rights reserved.

  7. Direct ultrasound-assisted extraction and characterization of phenolic compounds from fresh houseleek (Sempervivum marmoreum L. leaves

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    Karabegović Ivana T.

    2018-01-01

    Full Text Available The effects of ultrasound power and frequency on the yield of total extractive substances (TES, total phenolic content (TPC, total flavonoid content (TFC and antioxidant activity (AOA of fresh houseleek leaves extracts obtained by direct ultrasound-assisted extraction (DUAE were studied. Preliminary extraction of plant material was performed using methanol, acetone and 2-propanol by Soxhlet extraction. It was found that maximum TES yield could be obtained by methanol extraction (2.91±0.02, followed by acetone and 2-propanol with a TES yield of 2.32±0.01 and 2.01±0.03 g per 100 g of fresh plant material, respectively. In the fresh houseleek leaves extracts obtained by DUAE and methanol as the chosen solvent, TPC, TFC and AOA were in the ranges of: 40.5–85.9 mg gallic acid/g dry extract, 12.7–19.3 mg rutin/g dry extract and 24.6–108.2μg/ml, respectively. The results showed that the increase in the ultrasound power and extraction time have positive and significant (p < 0.05 effects on the TPC, TFC and AOA, while the increase in the ultrasound frequency leads to a decrease in the TPC, TFC and AOA of the extracts. A chromatographic analysis of crude extract identified the following: kaempferol 3-O-(6’’-O-malonylglucoside- 7-O-glucosyde, kaempferol 3-O-glucoside-7-O-rhamnoside, luteolin 5-O-(6’’-O-malonylglucoside, kaempferol 3-O-(6’’-O-acetylglucoside-7-O-rhamnoside, genkwanin 5-O-glucoside, luteolin 5-O-(6’’-O-malonylglucoside, kaempferol 3-O-(6’’-O-malonylglucoside, kaempferol 3-O-rhamnoside, quercetin, genkwanin 4’-O-glucoside and hyperoside. [Project of the Serbian Ministry of Education, Science and Technological Development, Grant no. 172047

  8. Red onion scales ameliorated streptozotocin-induced diabetes and diabetic nephropathy in Wistar rats in relation to their metabolite fingerprint.

    Science.gov (United States)

    Abouzed, Tarek Kamal; Contreras, María Del Mar; Sadek, Kadry Mohamed; Shukry, Moustafa; H Abdelhady, Doaa; Gouda, Wael Mohamed; Abdo, Walied; Nasr, Nasr Elsayed; Mekky, Reham Hassan; Segura-Carretero, Antonio; Kahilo, Khaled Abdel-Aleim; Abdel-Sattar, Essam

    2018-06-01

    The present study was designed to investigate the effect of red onion scales extract (ROS) against diabetic nephropathy, in relation to its metabolic profiling. Four groups of male Wistar rats were assigned as follows; 1st untreated group, 2nd group (animals with diabetes) treated with streptozotocin (STZ, 50 mg/kg) IP, 3rd group co-treated with ROS (150 mg/kg + STZ, 50 mg/kg) and 4th group co-treated with ROS by a dose (300 mg/kg + STZ, 50 mg/kg) daily. After four weeks, random and fasting blood glucose (FBG) levels, serum insulin, advanced glycation end products (AGEs), urea, uric acid and inflammatory and fibrotic gene expression were evaluated. Moreover, histopathological examination of the renal tissues was performed. In addition, the metabolic profiling of ROS was performed via RP-HPLC-DAD-QTOF-MS and -MS/MS. The metabolic profiling of ROS revealed that protocatechuic acid and cyanidin-3-O-glucoside were the predominant compounds among 32 metabolites identified in the extract. ROS treated groups showed improvement of FBG and AGEs levels, whereas serum insulin level showed significant elevation. In addition, down-regulation of inflammatory mRNA expression associated with the hyperglycemic condition and amelioration in histopathological alterations in kidney tissues were observed. This study displayed the presence of 32 phenolic compounds in the ethanolic extract of ROS, a common by-product of the industrial production of onion in Egypt. This study proved the therapeutic potential of ROS as antidiabetic agent and its preventive effect against diabetic nephropathy. Therefore, this study represents a perspective of the utilization of food waste products. Copyright © 2018 Elsevier B.V. All rights reserved.

  9. Determinants and Expansion of Specificity in a Trichothecene UDP-Glucosyltransferase from Oryza sativa.

    Science.gov (United States)

    Wetterhorn, Karl M; Gabardi, Kaitlyn; Michlmayr, Herbert; Malachova, Alexandra; Busman, Mark; McCormick, Susan P; Berthiller, Franz; Adam, Gerhard; Rayment, Ivan

    2017-12-19

    Family 1 UDP-glycosyltransferases (UGTs) in plants primarily form glucose conjugates of small molecules and, besides other functions, play a role in detoxification of xenobiotics. Indeed, overexpression of a barley UGT in wheat has been shown to control Fusarium head blight, which is a plant disease of global significance that leads to reduced crop yields and contamination with trichothecene mycotoxins such as deoxynivalenol (DON), T-2 toxin, and many other structural variants. The UGT Os79 from rice has emerged as a promising candidate for inactivation of mycotoxins because of its ability to glycosylate DON, nivalenol, and hydrolyzed T-2 toxin (HT-2). However, Os79 is unable to modify T-2 toxin (T-2), produced by pathogens such as Fusarium sporotrichioides and Fusarium langsethii. Activity toward T-2 is desirable because it would allow a single UGT to inactivate co-occurring mycotoxins. Here, the structure of Os79 in complex with the products UDP and deoxynivalenol 3-O-glucoside is reported together with a kinetic analysis of a broad range of trichothecene mycotoxins. Residues associated with the trichothecene binding pocket were examined by site-directed mutagenesis that revealed that trichothecenes substituted at the C4 position, which are not glycosylated by wild-type Os79, can be accommodated in the binding pocket by increasing its volume. The H122A/L123A/Q202L triple mutation, which increases the volume of the active site and attenuates polar contacts, led to strong and equivalent activity toward trichothecenes with C4 acetyl groups. This mutant enzyme provides the broad specificity required to control multiple toxins produced by different Fusarium species and chemotypes.

  10. Antinociceptive and Antibacterial Properties of Anthocyanins and Flavonols from Fruits of Black and Non-Black Mulberries

    Directory of Open Access Journals (Sweden)

    Hu Chen

    2017-12-01

    Full Text Available Anthocyanins and flavones are important pigments responsible for the coloration of fruits. Mulberry fruit is rich in anthocyanins and flavonols, which have multiple uses in traditional Chinese medicine. The antinociceptive and antibacterial activities of total flavonoids (TF from black mulberry (MnTF, TF of Morus nigra and non-black mulberry (MmTF, TF of Morus mongolica; and MazTF, TF of Morus alba ‘Zhenzhubai’ fruits were studied. MnTF was rich in anthocyanins (11.3 mg/g and flavonols (0.7 mg/g identified by ultra-performance liquid chromatography–tunable ultraviolet/mass single-quadrupole detection (UPLC–TUV/QDa. Comparatively, MmTF and MazTF had low flavonol contents and MazTF had no anthocyanins. MnTF showed significantly higher antinociceptive and antibacterial activities toward Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus than MmTF and MazTF. MnTF inhibited the expression of interleukin 6 (IL-6, inducible nitric oxide synthase (iNOS, phospho-p65 (p-p65 and phospho-IκBα (p-IκBα, and increased interleukin 10 (IL-10. Additionally, mice tests showed that cyanidin-3-O-glucoside (C3G, rutin (Ru and isoquercetin (IQ were the main active ingredients in the antinociceptive process. Stronger antinociceptive effect of MnTF was correlated with its high content of anthocyanins and flavonols and its inhibitory effects on proinflammatory cytokines, iNOS and nuclear factor-κB (NF-κB pathway-related proteins.

  11. Unravelling the bioherbicide potential of Eucalyptus globulus Labill: Biochemistry and effects of its aqueous extract.

    Directory of Open Access Journals (Sweden)

    Carolina G Puig

    Full Text Available In the worldwide search for new strategies in sustainable weed management, the use of plant species able to produce and release phytotoxic compounds into the environment could be an effective alternative to synthetic herbicides. Eucalyptus globulus Labill. is known to be a source of biologically active compounds responsible for its phytotoxic and allelopathic properties. Our previous results demonstrated the bioherbicide potential of eucalyptus leaves incorporated into the soil as a green manure, probably through the release of phytotoxins into the soil solution. Thus, the aims of this study were to understand the phytotoxicity of the eucalyptus leaves aqueous extract applied in pre- and post-emergence, and to identify and quantify its potentially phytotoxic water-soluble compounds. The effects were tested on the germination and early growth of the model target species Lactuca sativa and Agrostis stolonifera, and on physiological parameters of L. sativa adult plants after watering or spraying application. Dose-response curves and ED50 and ED80 values for eucalyptus aqueous extracts revealed pre-emergence inhibitory effects on both target species, effects being comparable to the herbicide metolachlor. While spraying treatment reduced the aerial and root biomass and increased the dry weight/fresh weight ratio of lettuce adult plants, watering application reduced protein contents and chlorophyll concentrations with respect to control, reflecting different modes of action depending on the site of phytotoxin entry. Via HPLC analyses, a total of 8 phenolic compounds (chlorogenic, two ρ-coumaric derivatives, ellagic, hyperoside, rutin, quercitrin, and kaempferol 3-O-glucoside and other 5 low weight organic acids (citric, malic, shikimic, succinic and fumaric acids were obtained from aqueous extract, the latter being identified for the first time in E. globulus. Despite some phytotoxic effects were found on lettuce adult plants, the use of eucalyptus

  12. Metabolite profiling of tomato (Lycopersicon esculentum) using 1H NMR spectroscopy as a tool to detect potential unintended effects following a genetic modification.

    Science.gov (United States)

    Le Gall, Gwénaëlle; Colquhoun, Ian J; Davis, Adrienne L; Collins, Geoff J; Verhoeyen, Martine E

    2003-04-23

    The maize transcription factors LC and C1 were simultaneously overexpressed in tomato with the aim of producing lines with increased amounts of flavonols. The metabolite composition of these genetically modified tomatoes has been compared with that of azygous (nonmodified) controls grown side-by-side under the same conditions. It has been possible to observe metabolic changes in both types at different stages of maturity. (1)H NMR spectra showed that the levels of glutamic acid, fructose, and some nucleosides and nucleotides gradually increase from the immature to the ripe stage, whereas some amino acids such as valine and gamma-aminobutyric acid were present in higher amounts in unripe tomatoes. Apart from the significantly increased content of six main flavonoid glycosides (mainly kaempferol-3-O-rutinoside, with additional increases in kaempferol-3,7-di-O-glucoside (1), kaempferol-3-O-rutinoside-7-O-glucoside (2), kaempferol-3-O-glucoside, a dihydrokaempferol-O-hexoside (3), and naringenin-7-O-glucoside), the levels of at least 15 other metabolites were found to be different between the two types of red tomato. Among them were citric acid, sucrose, phenylalanine, and trigonelline. However, although statistically significant, these changes in mean values were relatively minor (less than 3-fold) and within the natural variation that would be observed in a field-grown crop. Nevertheless, this study clearly showed that NMR combined with chemometrics and univariate statistics can successfully trace even small differences in metabolite levels between plants and therefore represents a powerful tool to detect potential unintended effects in genetically modified crops.

  13. Changes in polyphenols of the seed coat during the after-darkening process in pinto beans (Phaseolus vulgaris L.).

    Science.gov (United States)

    Beninger, Clifford W; Gu, Liwei; Prior, Ronald L; Junk, Donna C; Vandenberg, Albert; Bett, Kirstin E

    2005-10-05

    Proanthocyanidins and flavonoids were isolated and identified from seed coats of two aged and nonaged pinto bean lines: 1533-15 and CDC Pintium. The seed coat of 1533-15 darkens slowly and never darkens to the same extent as CDC Pintium. Analysis of the overall level of proanthocyanidins using a vanillin assay demonstrated that aged and nonaged seed coats of CDC Pintium had significantly higher levels of proanthocyanidins than aged and nonaged 1533-15 seed coats. Aged and nonaged seed coats of both lines were found to contain one main flavonol monomer, kaempferol, and three minor flavonols, kaempferol 3-O-glucoside, kaempferol 3-O-glucosylxylose, and kaempferol 3-O-acetylglucoside. These compounds were identified by NMR and ESI-MS analysis (except for kaempferol 3-O-acetylglucoside, which was tentatively identified only by ESI-MS analysis) and quantified using HPLC-DAD. The combined concentrations of all the kaempferol compounds in seed coats of CDC Pintium were significantly higher than in seed coats of 1533-15, and the combined contents did not change after aging. The content of kaempferol decreased nearly by half in the seed coats of CDC Pintium after aging, whereas no significant change was observed in the seed coats of 1533-15. Proanthocyanidin fractions from both lines, aged and nonaged, were subjected to LC-MS/MS analysis and found to be composed primarily of procyanidins. Procyanidins in the seed coats were predominantly polymers with the degree of polymers higher than 10. The proportion of these polymers decreased after aging, while that of the low-molecular-weight procyanidins increased. A catechin-kaempferol adduct was tentatively identified in both lines by LC-MS/MS, and the concentration increased in the seed coats after aging.

  14. Effect of gamma irradiation on the pigments and the biological activities of methanolic extracts from leaves of centipedegrass (Eremochloa ophiuroides Munro)

    International Nuclear Information System (INIS)

    Lee, Eun Mi; Lee, Seung Sik; Bai, Hyoung-Woo; Cho, Jae-Young; Kim, Tae Hoon; Chung, Byung Yeoup

    2013-01-01

    Extracts from centipedegrass (Eremochloa ophiuroides Munro) have been previously identified as having beneficial effects medically and cosmetically. In this study, the effects of gamma irradiation on pigment removal and biological activities of centipedegrass extracts to promote industrial application were investigated. The methanolic extracts were exposed to gamma irradiation at dose ranging from 2 to 20 kGy. The major pigments of centipedegrass extracts, cyanidin-3-O-glucoside and cyanidin-3-O-(6″-malonyl-)glucoside, were found to be effectively removed by gamma irradiation above 10 kGy. Although the reddish-orange color of the cyanidins was markedly decreased by gamma irradiation, the biological activities were relatively unaffected. The biological activities such as 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity, inhibition of tyrosinase activity, and inhibition of elastase activity in methanolic extracts were modulated from 50.5% to 70.2%, from 50.9% to 65.8% and from 65.6% to 94.0%, respectively. Surprisingly, the biological activities have the highest activities after 6–8 kGy of gamma irradiation. These results indicate that despite pigment degradation, biological activities were maintained or increased by gamma irradiation. Based on these results, gamma irradiation may be a useful tool to remove the undesirable reddish-orange color present in centipedegrass without any loss of biological activities, thereby promoting its utility in industrial applications such as manufacturing of cosmetic products. - Highlights: • The pigments of centipedegrass extracts were decreased by gamma irradiation. • The contents of maysin and its derivatives were slightly changed by gamma irradiation. • The biological activities of centipedegrass extracts were retained or increased by gamma irradiation

  15. Unravelling the bioherbicide potential of Eucalyptus globulus Labill: Biochemistry and effects of its aqueous extract

    Science.gov (United States)

    Reigosa, Manuel J.; Valentão, Patrícia; Andrade, Paula B.

    2018-01-01

    In the worldwide search for new strategies in sustainable weed management, the use of plant species able to produce and release phytotoxic compounds into the environment could be an effective alternative to synthetic herbicides. Eucalyptus globulus Labill. is known to be a source of biologically active compounds responsible for its phytotoxic and allelopathic properties. Our previous results demonstrated the bioherbicide potential of eucalyptus leaves incorporated into the soil as a green manure, probably through the release of phytotoxins into the soil solution. Thus, the aims of this study were to understand the phytotoxicity of the eucalyptus leaves aqueous extract applied in pre- and post-emergence, and to identify and quantify its potentially phytotoxic water-soluble compounds. The effects were tested on the germination and early growth of the model target species Lactuca sativa and Agrostis stolonifera, and on physiological parameters of L. sativa adult plants after watering or spraying application. Dose-response curves and ED50 and ED80 values for eucalyptus aqueous extracts revealed pre-emergence inhibitory effects on both target species, effects being comparable to the herbicide metolachlor. While spraying treatment reduced the aerial and root biomass and increased the dry weight/fresh weight ratio of lettuce adult plants, watering application reduced protein contents and chlorophyll concentrations with respect to control, reflecting different modes of action depending on the site of phytotoxin entry. Via HPLC analyses, a total of 8 phenolic compounds (chlorogenic, two ρ-coumaric derivatives, ellagic, hyperoside, rutin, quercitrin, and kaempferol 3-O-glucoside) and other 5 low weight organic acids (citric, malic, shikimic, succinic and fumaric acids) were obtained from aqueous extract, the latter being identified for the first time in E. globulus. Despite some phytotoxic effects were found on lettuce adult plants, the use of eucalyptus aqueous extract

  16. HPLC-UV/DAD and ESI-MS(n) analysis of flavonoids and antioxidant activity of an Algerian medicinal plant: Paronychia argentea Lam.

    Science.gov (United States)

    Sait, Sabrina; Hamri-Zeghichi, Sabrina; Boulekbache-Makhlouf, Lila; Madani, Khodir; Rigou, Peggy; Brighenti, Virginia; Pio Prencipe, Francesco; Benvenuti, Stefania; Pellati, Federica

    2015-01-01

    Paronychia argentea Lam., belonging to the Caryophyllaceae family, is a perennial plant widely distributed in Algeria. Even though this plant is used in the Algerian popular medicine, its phytochemical characterization is incomplete. In this study, the flavonoid profile and the in vitro antioxidant activity of the ethanolic extract, decoction and infusion of P. argentea aerial parts are reported. Flavonoids were analyzed by means of high-performance liquid chromatography coupled with diode array detection and electrospray ionization mass spectrometry. Eleven compounds were identified and six of them, including isorhamnetin-3-O-dihexoside, quercetin-3-O-glucoside, quercetinmethylether-O-hexoside, quercetin, jaceosidin and isorhamnetin, were described in this plant for the first time. The ethanol extract showed the highest flavonoid content, followed by the decoction and the infusion (25.4 ± 0.8 mg/g of DM, 8.4 ± 0.5 mg/g of DM, 0.2 mg/g of DM, respectively), while the best antioxidant activity was shown by the decoction (RC0.5 = 178 μg/mL for reducing power, 72.4% of inhibition of lipid peroxidation, IC50 = 27.38μ g/mL for DPPH radical scavenging activity and 59.7% of inhibition of NO radical). These results showed that P. argentea decoction could be considered as a valuable source of flavonoids and antioxidants that might contribute to the valorization of the phytotherapeutic potential of this plant. Copyright © 2015 Elsevier B.V. All rights reserved.

  17. Antioxidant activity, the content of total phenols and flavonoids in the ethanol extracts of Mentha longifolia (L. Hudson dried by the use of different techniques

    Directory of Open Access Journals (Sweden)

    Stanisavljević Dragana M.

    2012-01-01

    Full Text Available In this study, we have examined the yield of extracted substances obtained by means of extraction using 70 % ethanol (v/v, the content of total phenols and flavonoids, as well as the antioxidant activity of the extracts obtained from the samples of the herbs dried by means of different techniques. Wild mint Mentha longifolia (L. Hudson was dried naturally in a laboratory oven at a temperature of 45 °C and in an absorptive low temperature condensation oven at 35°C. The highest yield of extracts was obtained from the naturally dried herbs and the lowest from the herbs dried in the low temperature condensation drying oven. The content of total phenols and flavonoids was determined by spectrophotometric methods with an FC reagent and by the complexation reaction with aluminium-chloride, respectively. The extract of the naturally dried herbs had the highest overall content of phenols (113.8±2.0 mg of gallic acid/g of the dry extract and flavonoids (106.7±0.3 mg of rutin/g of the dry extract. The highest antioxidant activity determined by the FRAP and DPPH assay was determined in the extracts obtained from naturally dried herbs (2.76±0.15 mmol Fe2+/mg of the dry extract and EC50=0.022±0.001 mg/ml, while the lowest was obtained from the extracts of herbs dried in the laboratory oven (1.13±0.11 mmol Fe2+/mg of the dry extract and EC50=0.033±0.001 mg/ml. The HPLC-DAD analysis result show that the greatest content of phenolic compounds show extract obtained from naturally dried plant material. The dominant phenolic component in the all extracts is Kaempferol 3-O-glucoside. The content of all phenolic compound strongly depend on the drying conditions.

  18. Flavonoids from the flowers of Impatiens glandulifera Royle isolated by high performance countercurrent chromatography.

    Science.gov (United States)

    Vieira, Mariana N; Winterhalter, Peter; Jerz, Gerold

    2016-01-01

    Impatiens glandulifera Royle (Balsaminaceae) is an annual herb from the Himalaya region, currently widespread along European river systems and one of the most important neophyte invading plants in Germany. Exploring the effects of allelopathic plant chemicals is important for the understanding of its ecological impacts in the process of suppression of indigenous plant species. To investigate the chemical composition of Impatiens glandulifera flowers (IGFs) using high performance countercurrent chromatography (HPCCC). The flowers of Impatiens glandulifera were manually separated and extracted with ethanol. LC-ESI-MS/MS was used to characterise the crude extract of IGF. The various flavonoids detected were isolated by HPCCC using of methyl tert-butyl ether-acetonitrile-water (2:2:3, v/v/v). The combination of the data provided by preparative ESI-MS/MS metabolite profiling, LC-ESI-MS/MS, UV-vis and 1D/2D-NMR spectroscopic analysis was used to elucidate the structures of the isolated compounds. HPCCC runs led to the direct isolation of pure dihydromyricetin (ampelopsin), eriodictyol-7-O-glucoside, kaempferol-3-O-glucoside (astragalin) and kaempferol-3-O-6"-malonyl-glucoside, as well as the pre-purification of kaempferol-3-O-rhamno-rhamnosyldiglucoside, quercetin-3-O-galactoside (hyperoside), quercetin and kaempferol in a single step. This is the first report on the flavonoid composition of the species Impatiens glandulifera. The developed protocol was successfully used to isolate the main flavonoids from the crude extract of IGFs. This combined HPCCC and HPLC procedure could be applied to the fast fractionation and recovery of flavonoid derivatives of other plant extracts. Copyright © 2016 John Wiley & Sons, Ltd.

  19. THE PHENOLIC COMPOSITION OF THE HEPATOPROTECTIVE AND ANTIOXIDANT FRACTIONS OF Albizia lebbeck L.

    Directory of Open Access Journals (Sweden)

    Nadia M. Sokkar

    Full Text Available An investigation of the hepatoprotective and antioxidant activities of the chloroform, ethyl acetate and n-butanol fractions of the leaves of Albizia lebbeck L. was performed. The first two fractions expressed the best results regarding the suppression of the increased levels of plasma amino-transferases and alkaline phosphatase in liver-damaged mice (after intoxication with CCl4 compared with silymarin and the significantly increased GSH content of alloxan- induced diabetic rats compared with vitamin E (tests and reference drugs were orally administered. The bioactive fractions of Albizia lebbeck L. were subjected to chromatographic analysis to investigate their phenolic contents using a HPLC-PDA-ESI-MS/MS technique in the negative ion mode. The results constitute the first report of the presence of seven compounds in the genus Albizia, three of which were identified as 3-O-caffeoylquinic acid, cafeic acid, myricetin; four other flavonoids (in mg 100 g-1 dry powder ± SD, myricetin 3-O-rhamnoside (0.129 ± 0.0052, quercetin 3-O-dideoxypentoside (0.011 ± 0.001, kaempferol 3-O-glucoside (0.015 ± 0.002, quercetin 3-O-dihexoside (0.138 ± 0.002; quercetin 3-O-rutinoside at a level of 0.135 ± 0.004; and the aglycones quercetin, luteolin and kaempferol. Method validation was performed, providing an analytical technique that can be used to detect trace amounts of the identified compounds in Albizia extracts with rapid sample preparation.

  20. Qualitative Analysis of Polyphenols in Macroporous Resin Pretreated Pomegranate Husk Extract by HPLC-QTOF-MS.

    Science.gov (United States)

    Abdulla, Rahima; Mansur, Sanawar; Lai, Haizhong; Ubul, Ablikim; Sun, Guangying; Huang, Guozheng; Aisa, Haji Akber

    2017-09-01

    Pomegranate (Punica granatum L.) husk is a traditional herbal medicine abundant in phenolic compounds and plays some roles in the treatment of oxidative stress, bacterial and viral infection, diabetes mellitus, and acute and chronic inflammation. Identification and determination of polyphenols in macroporous resin pretreated pomegranate husk extract by high performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (HPLC-QTOF-MS). The total polyphenols of pomegranate husk were prepared by ethanol extraction followed by pretreatment with HPD-300 macroporous resin. The polyphenolic compounds were qualitatively analysed by HPLC-QTOF-MS in negative electrospray ionisation (ESI) mode at different collision energy (CE) values. A total of 50 polyphenols were detected in the extract of pomegranate husk, including 35 hydrolysable tannins and 15 flavonoids with distinct retention time, fragmentation behaviours and characteristics, and the accurate mass-to-charge ratios at low, moderate and high CE values. Of these, we identified nine compounds for the first time in the pomegranate husk, including hexahydroxydiphenoyl-valoneoyl-glucoside (HHDP-valoneyl-glucoside), galloyl-O-punicalin, rutin, hyperoside, quercimeritrin, kaempferol-7-O-rhahmano-glucoside, luteolin-3'-O-arabinoside, luteolin-3'-O-glucoside, and luteolin-4'-O-glucoside. To validate the specificity and accuracy of mass spectrometry in the detection of polyphenols, as compared to the fragmentation pathways of granatin B in detail, including the HHDP-valoneyl- glucoside was first identified from pomegranate husk. The study provides evidence for the quality control and development of novel drugs based on polyphenols from the pomegranate husk. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

  1. Tc-MYBPA an Arabidopsis TT2-like transcription factor and functions in the regulation of proanthocyanidin synthesis in Theobroma cacao.

    Science.gov (United States)

    Liu, Yi; Shi, Zi; Maximova, Siela N; Payne, Mark J; Guiltinan, Mark J

    2015-06-25

    The flavan-3-ols catechin and epicatechin, and their polymerized oligomers, the proanthocyanidins (PAs, also called condensed tannins), accumulate to levels of up to 15 % of the total weight of dry seeds of Theobroma cacao L. These compounds have been associated with several health benefits in humans. They also play important roles in pest and disease defense throughout the plant. In Arabidopsis, the R2R3 type MYB transcription factor TT2 regulates the major genes leading to the synthesis of PA. To explore the transcriptional regulation of the PA synthesis pathway in cacao, we isolated and characterized an R2R3 type MYB transcription factor MYBPA from cacao. We examined the spatial and temporal gene expression patterns of the Tc-MYBPA gene and found it to be developmentally expressed in a manner consistent with its involvement in PAs and anthocyanin synthesis. Functional complementation of an Arabidopsis tt2 mutant with Tc-MYBPA suggested that it can functionally substitute the Arabidopsis TT2 gene. Interestingly, in addition to PA accumulation in seeds of the Tc-MYBPA expressing plants, we also observed an obvious increase of anthocyanidin accumulation in hypocotyls. We observed that overexpression of the Tc-MYBPA gene resulted in increased expression of several key genes encoding the major structural enzymes of the PA and anthocyanidin pathway, including DFR (dihydroflavanol reductase), LDOX (leucoanthocyanidin dioxygenase) and BAN (ANR, anthocyanidin reductase). We conclude that the Tc-MYBPA gene that encodes an R2R3 type MYB transcription factor is an Arabidopsis TT2 like transcription factor, and may be involved in the regulation of both anthocyanin and PA synthesis in cacao. This research may provide molecular tools for breeding of cacao varieties with improved disease resistance and enhanced flavonoid profiles for nutritional and pharmaceutical applications.

  2. Blotting Assisted by Heating and Solvent Extraction for DESI-MS Imaging

    Science.gov (United States)

    Cabral, Elaine C.; Mirabelli, Mario F.; Perez, Consuelo J.; Ifa, Demian R.

    2013-06-01

    Imprints of potato sprout ( Solanum tuberosum L.), gingko leaves (Gingko biloba L. ) and strawberries (Fragaria x ananassa Duch. ) were successfully imaged by desorption electrospray ionization mass spectrometry (DESI-MS) on TLC plates through blotting assisted by heating and/or solvent extraction. Ion images showing the distribution of significant compounds such as glycoalkaloid toxins in potato sprout, ginkgolic acids and flavonoids in ginkgo leaves, and sugars and anthocyanidin in strawberry were obtained. Practical implications of this work include analysis of a wide range of irregular or soft materials by different imprinting conditions without requiring the addition of matrices or use of specific kinds of surfaces.

  3. Overexpression of PtrMYB119, a R2R3-MYB transcription factor from Populus trichocarpa, promotes anthocyanin production in hybrid poplar.

    Science.gov (United States)

    Cho, Jin-Seong; Nguyen, Van Phap; Jeon, Hyung-Woo; Kim, Min-Ha; Eom, Seok Hyun; Lim, You Jin; Kim, Won-Chan; Park, Eung-Jun; Choi, Young-Im; Ko, Jae-Heung

    2016-09-01

    Anthocyanins are a group of colorful and bioactive natural pigments with important physiological and ecological functions in plants. We found an MYB transcription factor (PtrMYB119) from Populus trichocarpa that positively regulates anthocyanin production when expressed under the control of the CaMV 35S promoter in transgenic Arabidopsis Amino acid sequence analysis revealed that PtrMYB119 is highly homologous to Arabidopsis PAP1 (PRODUCTION OF ANTHOCYANIN PIGMENT1), a well-known transcriptional activator of anthocyanin biosynthesis. Independently produced transgenic poplars overexpressing PtrMYB119 or PtrMYB120 (a paralogous gene to PtrMYB119) (i.e., 35S::PtrMYB119 and 35S::PtrMYB120, respectively) showed elevated accumulation of anthocyanins in the whole plants, including leaf, stem and even root tissues. Using a reverse-phase high-performance liquid chromatography, we confirmed that the majority of the accumulated anthocyanin in our transgenic poplar is cyanidin-3-O-glucoside. Gene expression analyses revealed that most of the genes involved in the anthocyanin biosynthetic pathway were highly upregulated in 35S::PtrMYB119 poplars compared with the nontransformed control poplar. Among these genes, expression of PtrCHS1 (Chalcone Synthase1) and PtrANS2 (Anthocyanin Synthase2), which catalyze the initial and last steps of anthocyanin biosynthesis, respectively, was upregulated by up to 350-fold. Subsequent transient activation assays confirmed that PtrMYB119 activated the transcription of both PtrCHS1 and PtrANS2 Interestingly, expression of MYB182, a repressor of both anthocyanin and proanthocyanidin (PA) biosynthesis, was largely suppressed in 35S::PtrMYB119 poplars, while expression of MYB134, an activator of PA biosynthesis, was not changed significantly. More interestingly, high-level accumulation of anthocyanins in 35S::PtrMYB119 poplars did not have an adverse effect on plant growth. Taken together, our results demonstrate that PtrMYB119 and PtrMYB120

  4. High performance liquid chromatography analysis of anthocyanins in bilberries (Vaccinium myrtillus L.), blueberries (Vaccinium corymbosum L.), and corresponding juices.

    Science.gov (United States)

    Müller, Dolores; Schantz, Markus; Richling, Elke

    2012-04-01

    In the present study the anthocyanin content of commercially available bilberry juices and fresh fruits were quantified by using 15 authentic anthocyanin standards via high performance liquid chromatography with an ultra-violet detector (HPLC-UV/VIS). Delphinidin-3-O-glucopyranoside, delphinidin-3-O-galactopyranoside, and cyanidin-3-O-arabinopyranoside were the major anthocyanins found in juices, nectar, and fresh bilberries. In contrast, fresh blueberries had higher concentrations of malvidin-3-O-arabinopyranoside and petunidin-3-O-galactopyranoside. Up to 438 mg anthocyanins per 100 g fresh weight (2762 mg/100 g dry weight (DW)) were detected in blueberries from various sources, whereas bilberries contained a maximum of 1017 mg anthocyanins per 100 g fresh weight (7465 mg/100 g DW). Commercially available bilberry and blueberry juices (n= 9) as well as nectars (n= 4) were also analyzed. Anthocyanin concentrations of juices (1610 mg/L to 5963 mg/L) and nectar from bilberries (656 mg/L to 1529 mg/L) were higher than those of blueberry juices (417 mg/L) and nectar (258 mg/L to 386 mg/L). We conclude that using several authentic anthocyanin references to quantify anthocyanin contents indicated them to be up to 53% and 64% higher in fresh bilberries and blueberries, respectively, than previously reported using cyanidin-3-O-glucoside. This study has also demonstrated that commercially available juices produced from bilberries contain much higher anthocyanin concentrations than those from blueberries. We have investigated the contents of a special class of antioxidants, namely anthocyanins in blueberry and billberry fruits and juices commercially available in Germany. To achieve reliable data we have used authentic standards for the first time. We think that our results are important in the field of nutritional intake of this important class of polyphenols and fruit juice companies get a closer insight in the occurrence of these antioxidants in market samples to be used

  5. Antioxidant activity and phenolic profile of pistachio (Pistacia vera L., variety Bronte) seeds and skins.

    Science.gov (United States)

    Tomaino, Antonio; Martorana, Maria; Arcoraci, Teresita; Monteleone, Domenico; Giovinazzo, Corrado; Saija, Antonella

    2010-09-01

    Pistachio (Pistacia vera L.; Anacardiaceae) is native of aride zones of Central and West Asia and distributed throughout the Mediterranean basin. In Italy, a pistachio cultivar of high quality is typical of Bronte (Sicily), an area around the Etna volcano, where the lava land and climate allow the production of a nut with intense green colour and aromatic taste, very appreciated in international markets. Pistachio nuts are a rich source of phenolic compounds, and have recently been ranked among the first 50 food products highest in antioxidant potential. Pistachio nuts are often used after removing the skin, which thus represents a significant by-product of pistachio industrial processing. The present study was carried out to better characterize the phenolic composition and the antioxidant activity of Bronte pistachios, with the particular aim to evaluate the differences between pistachio seeds and skins. The total content of phenolic compounds in pistachios was shown to be significantly higher in skins than in seeds. By HPLC analysis, gallic acid, catechin, eriodictyol-7-O-glucoside, naringenin-7-O-neohesperidoside, quercetin-3-O-rutinoside and eriodictyol were found both in pistachio seeds than in skins; furthermore, genistein-7-O-glucoside, genistein, daidzein and apigenin appeared to be present only in pistachio seeds, while epicatechin, quercetin, naringenin, luteolin, kaempferol, cyanidin-3-O-galactoside and cyanidin-3-O-glucoside are contained only in pistachio skins. The antioxidant activity of pistachio seeds and skins were determined by means of four different assays (DPPH assay, Folin-Ciocalteau colorimetric method and TEAC assay, SOD-mimetic assay). As expected on the basis of the chemical analyses, pistachio skins have shown to possess a better activity with respect to seeds in all tests. The excellent antioxidant activity of pistachio skins can be explained by its higher content of antioxidant phenolic compounds. By HPLC-TLC analysis, gallic acid

  6. Maize Lc transcription factor enhances biosynthesis of anthocyanins, distinct proanthocyanidins and phenylpropanoids in apple (Malus domestica Borkh.).

    Science.gov (United States)

    Li, Houhua; Flachowsky, Henryk; Fischer, Thilo C; Hanke, Magda-Viola; Forkmann, Gert; Treutter, Dieter; Schwab, Wilfried; Hoffmann, Thomas; Szankowski, Iris

    2007-10-01

    Flavonoids are a large family of polyphenolic compounds with manifold functions in plants. Present in a wide range of vegetables and fruits, flavonoids form an integral part of the human diet and confer multiple health benefits. Here, we report on metabolic engineering of the flavonoid biosynthetic pathways in apple (Malus domestica Borkh.) by overexpression of the maize (Zea mays L.) leaf colour (Lc) regulatory gene. The Lc gene was transferred into the M. domestica cultivar Holsteiner Cox via Agrobacterium tumefaciens-mediated transformation which resulted in enhanced anthocyanin accumulation in regenerated shoots. Five independent Lc lines were investigated for integration of Lc into the plant genome by Southern blot and PCR analyses. The Lc-transgenic lines contained one or two Lc gene copies and showed increased mRNA levels for phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS), flavanone 3 beta-hydroxylase (FHT), dihydroflavonol 4-reductase (DFR), leucoanthocyanidin reductases (LAR), anthocyanidin synthase (ANS) and anthocyanidin reductase (ANR). HPLC-DAD and LC-MS analyses revealed higher levels of the anthocyanin idaein (12-fold), the flavan 3-ol epicatechin (14-fold), and especially the isomeric catechin (41-fold), and some distinct dimeric proanthocyanidins (7 to 134-fold) in leaf tissues of Lc-transgenic lines. The levels of phenylpropanoids and their derivatives were only slightly increased. Thus, Lc overexpression in Malus domestica resulted in enhanced biosynthesis of specific flavonoid classes, which play important roles in both phytopathology and human health.

  7. De novo biosynthesis of anthocyanins in Saccharomyces cerevisiae.

    Science.gov (United States)

    Eichenberger, Michael; Hansson, Anders; Fischer, David; Dürr, Lara; Naesby, Michael

    2018-06-01

    Anthocyanins (ACNs) are plant secondary metabolites responsible for most of the red, purple and blue colors of flowers, fruits and vegetables. They are increasingly used in the food and beverage industry as natural alternative to artificial colorants. Production of these compounds by fermentation of microorganisms would provide an attractive alternative. In this study, Saccharomyces cerevisiae was engineered for de novo production of the three basic anthocyanins, as well as the three main trans-flavan-3-ols. Enzymes from different plant sources were screened and efficient variants found for most steps of the biosynthetic pathway. However, the anthocyanidin synthase was identified as a major obstacle to efficient production. In yeast, this enzyme converts the majority of its natural substrates leucoanthocyanidins into the off-pathway flavonols. Nonetheless, de novo biosynthesis of ACNs was shown for the first time in yeast and for the first time in a single microorganism. It provides a framework for optimizing the activity of anthocyanidin synthase and represents an important step towards sustainable industrial production of these highly relevant molecules in yeast.

  8. Expression of Key Structural Genes of the Phenylpropanoid Pathway Associated with Catechin Epimerization in Tea Cultivars

    Directory of Open Access Journals (Sweden)

    Changsong Chen

    2017-05-01

    Full Text Available Catechin epimerization is an important factor affecting tea catechin compositions and thereby tea quality. However, a lack of tea germplasms with high non-epicatechins limits relative research. Here, a tea cultivar Y510 with high non-epicatechins was firstly reported and used for catechin and RNA sequencing (RNA-Seq analysis. Results showed that the (--gallocatechin gallate and (+-catechin (C contents in Y510 were at least 136 and 6 times higher than those in Fudingdabaicha and 0306I, but the epicatechins (--epigallocatechin and (--epicatechin (EC were significantly lower. Eleven unigenes potentially involved in catechin epimerization were identified by RNA-Seq analysis. Based on a combination of catechin and gene expression analysis, it was hypothesized that two anthocyanidin reductase genes (CsANR1, CsANR2 and an anthocyanidin synthase gene (CsANS are the key genes affecting catechin epimerization in tea. Non-epicatechin formations were hypothesized to be mainly influenced by the expression ratio of CsANR2 to CsANR1 and the expression of CsANS. Overexpression of CsANS in an Arabidopsis mutant tds4-2 led to a significant increase of EC accumulation in seeds, revealing CsANS is important for catechin epimerization. These results shed new light on breeding tea cultivars with special catechin compositions.

  9. Flavonoids, Flavonoid Subclasses, and Esophageal Cancer Risk: A Meta-Analysis of Epidemiologic Studies.

    Science.gov (United States)

    Cui, Lingling; Liu, Xinxin; Tian, Yalan; Xie, Chen; Li, Qianwen; Cui, Han; Sun, Changqing

    2016-06-08

    Flavonoids have been suggested to play a chemopreventive role in carcinogenesis. However, the epidemiologic studies assessing dietary intake of flavonoids and esophageal cancer risk have yielded inconsistent results. This study was designed to examine the association between flavonoids, each flavonoid subclass, and the risk of esophageal cancer with a meta-analysis approach. We searched for all relevant studies with a prospective cohort or case-control study design published from January 1990 to April 2016, using PUBMED, EMBASE, and Web of Science. Pooled odds ratios (ORs) were calculated using fixed or random-effect models. In total, seven articles including 2629 cases and 481,193 non-cases were selected for the meta-analysis. Comparing the highest-intake patients with the lowest-intake patients for total flavonoids and for each flavonoid subclass, we found that anthocyanidins (OR = 0.60, 95% CI: 0.49-0.74), flavanones (OR = 0.65, 95% CI: 0.49-0.86), and flavones (OR = 0.78, 95% CI 0.64-0.95) were inversely associated with the risk of esophageal cancer. However, total flavonoids showed marginal association with esophageal cancer risk (OR = 0.78, 95% CI: 0.59-1.04). In conclusion, our study suggested that dietary intake of total flavonoids, anthocyanidins, flavanones, and flavones might reduce the risk of esophageal cancer.

  10. Substituent Inductive Effects on the Electrochemical Oxidation of Flavonoids Studied by Square Wave Voltammetry and Ab Initio Calculations.

    Science.gov (United States)

    Arroyo-Currás, Netzahualcóyotl; Rosas-García, Víctor M; Videa, Marcelo

    2016-10-27

    Flavonoids are natural products commonly found in the human diet that show antioxidant, anti-inflammatory and anti-hepatotoxic activities. These nutraceutical properties may relate to the electrochemical activity of flavonoids. To increase the understanding of structure-electrochemical activity relations and the inductive effects that OH substituents have on the redox potential of flavonoids, we carried out square-wave voltammetry experiments and ab initio calculations of eight flavonoids selected following a systematic variation in the number of hydroxyl substituents and their location on the flavan backbone: three flavonols, three anthocyanidins, one anthocyanin and the flavonoid backbone flavone. We compared the effect that the number of -OH groups in the ring B of flavan has on the oxidation potential of the flavonoids considered, finding linear correlations for both flavonols and anthocyanidins ( R 2 = 0.98 ). We analyzed the effects that position and number of -OH substituents have on electron density distributions via ab initio quantum chemical calculations. We present direct correlations between structural features and oxidation potentials that provide a deeper insight into the redox chemistry of these molecules.

  11. Roasting conditions for preserving cocoa flavan-3-ol monomers and oligomers: interesting behaviour of Criollo clones.

    Science.gov (United States)

    De Taeye, Cédric; Bodart, Marie; Caullet, Gilles; Collin, Sonia

    2017-09-01

    Cocoa bean roasting is important for creating the typical chocolate aroma through Maillard reactions, but it is also a key step deleterious to the polyphenol content and profile. Compared with usual roasting at 150 °C, keeping the beans for 30 min at 120 °C or for 1 h at 90 °C proved much better for preventing strong degradation of native P1, P2 and P3 flavan-3-ols in cocoa (shown for Forastero, Trinitatio and Criollo cultivars). Surprisingly, Cuban, Mexican and Malagasy white-seeded beans behaved atypically when roasted for 30 min at 150 °C, releasing a pool of catechin. Enantiomeric chromatographic separation proved that this pool contained mainly (-)-catechin issued from (-)-epicatechin by epimerisation. As the (-)-epicatechin content remained relatively constant through Criollo bean roasting, flavan-3-ol monomers must have been regenerated from oligomers. This emergence of (-)-catechin in Criollo beans only, reported here for the first time, could be due to increased flavan-3-ol monomer stability in the absence of anthocyanidin-derived products. The degradation rate of flavan-3-ols through roasting is higher in cocoa beans containing anthocyani(di)ns. The liberation of a pool of (-)-catechin when submitted to roasting at 150 °C allows to distinguish white-seeded cultivars. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

  12. Gene Expression Profiling Soybean Stem Tissue Early Response to Sclerotinia sclerotiorum and In Silico Mapping in Relation to Resistance Markers

    Directory of Open Access Journals (Sweden)

    Bernarda Calla

    2009-07-01

    Full Text Available White mold, caused by (Lib. de Bary, can be a serious disease of crops grown under cool, moist environments. In many plants, such as soybean [ (L. Merr.], complete genetic resistance does not exist. To identify possible genes involved in defense against this pathogen, and to determine possible physiological changes that occur during infection, a microarray screen was conducted using stem tissue to evaluate changes in gene expression between partially resistant and susceptible soybean genotypes at 8 and 14 hours post inoculation. RNA from 15 day-old inoculated plants was labeled and hybridized to soybean cDNA microarrays. ANOVA identified 1270 significant genes from the comparison between time points and 105 genes from the comparison between genotypes. Selected genes were classified into functional categories. The analyses identified changes in cell-wall composition and signaling pathways, as well as suggesting a role for anthocyanin and anthocyanidin synthesis in the defense against . In-silico mapping of both the differentially expressed transcripts and of public markers associated with partial resistance to white mold, provided evidence of several differentially expressed genes being closely positioned to white mold resistance markers, with the two most promising genes encoding a PR-5 and anthocyanidin synthase.

  13. Molecular cloning and biochemical characterization of the UDP-glucose: flavonoid 3-O-glucosyltransferase from Concord grape (Vitis labrusca).

    Science.gov (United States)

    Hall, Dawn; Yuan, Xiao Xin; Murata, Jun; De Luca, Vincenzo

    2012-02-01

    Glucosylation of anthocyanidin substrates at the 3-O-position is crucial for the red pigmentation of grape berries and wine. The gene that encodes the enzyme involved in this reaction has been cloned from Vitis labrusca cv. Concord, heterologously expressed, and the recombinant enzyme (rVL3GT) was characterized. VL3GT has 96% amino acid sequence identity with Vitis vinifera VV3GT and groups phylogenetically with several other flavonoid 3-O-glycosyltransferases. In vitro substrate specificity studies and kinetic analyses of rVL3GT indicate that this enzyme preferentially glucosylates cyanidin as compared with quercetin. Crude protein extracts from several Concord grape tissues were assayed for glucosyltransferase activity with cyanidin and quercetin as acceptor substrates. A comparison of the VL3GT activities toward with these substrates showed that the 3GT enzyme activity is consistent with the expression of VL3GT in these tissues and is coincident with the biosynthesis of anthocyanins in both location and developmental stages. Enzyme activities in grape mesocarp, pre-veraison exocarp, leaf, flower bud, and flower tissues glucosylated quercetin but not cyanidin at high rates, suggesting the presence of additional enzymes which are able to glucosylate the 3-O-position of flavonols with higher specificity than anthocyanidins. Copyright © 2011 Elsevier Ltd. All rights reserved.

  14. Phthalate exposure, flavonoid consumption and breast cancer risk among Mexican women.

    Science.gov (United States)

    Mérida-Ortega, Ángel; Hernández-Alcaraz, César; Hernández-Ramírez, Raúl U; García-Martínez, Angélica; Trejo-Valdivia, Belem; Salinas-Rodríguez, Aarón; Svensson, Katherine; Cebrián, Mariano E; Franco-Marina, Francisco; López-Carrillo, Lizbeth

    2016-11-01

    To evaluate if selected phthalate exposure and flavonoid intake interact on breast cancer (BC) risk. Interviews and urine samples were obtained from 233 women with histologically confirmed BC and 221 healthy controls matched by age and place of residence, from various states of northern Mexico. Urinary metabolites concentrations of diethyl phthalate (DEP), butyl benzyl phthalate (BBzP) and dioctyl phthalate (DOP) were determined by solid-phase extraction coupled with high-performance liquid chromatography/isotope dilution/tandem mass spectrometry. Using a semiquantitative food frequency questionnaire, consumption of five types of flavonoids (anthocyanidins, flavan-3-ols, flavanones, flavones and flavonols) was estimated according to three food groups: vegetables, fruits and legumes-oil seeds. A higher intake of anthocyanidins and flavan-3-ols (from vegetables), synergistically increased the negative association between BBzP and BC. No other significant flavonoid-phthalate multiplicative interactions on the risk for BC were found. The consumption of some flavonoids may interact with exposure to phthalates on the risk of BC. Epidemiological and underlying mechanisms information is still insufficient and requires further investigations. Copyright © 2016 Elsevier Ltd. All rights reserved.

  15. Potential natural sensitizers extracted from the skin of Canarium odontophyllum fruits for dye-sensitized solar cells

    Science.gov (United States)

    Lim, Andery; Kumara, N. T. R. N.; Tan, Ai Ling; Mirza, Aminul Huq; Chandrakanthi, R. L. N.; Petra, Mohammad Iskandar; Ming, Lim Chee; Senadeera, G. K. R.; Ekanayake, Piyasiri

    2015-03-01

    Possibility of use of dye extract from skin samples of a seasonal, indigenous fruit from Borneo, namely Canarium odontophyllum, in dye sensitized solar cells (DSSCs) are explored. Three main groups of flavonoid pigments are detected and these pigments exhibit different UV-vis absorption properties, and hence showing different light harvesting capabilities. When applied in DSSCs. The detected pigment constituents of the extract consist of aurone (maritimein), anthocyanidin (pelargonidin) and anthocyanidin (cyanidin derivatives). When tested in DSSC, the highest conversion efficiency of 1.43% is exhibited by cyanidin derivatives, and this is followed by conversion efficiencies of 0.51% and 0.79% for aurone and pelargonidin, respectively. It is shown that individual pigments, like cyanidin derivatives and pelargonidin, exhibit higher power conversion efficiency when compared to that of C.odontophyllum skin pigment mixture (with a conversion efficiency of only 0.68%). The results indicate a possibility of masking effects of the pigments when used as a mixture. The acidification of C.odontophyllum skin pigments with concentrated hydrochloric acid improves the conversion efficiency of the mixture from 0.68% to 0.99%. The discussion in this paper will draw data and observations from the variation in absorption and adsorption properties, the HOMO-LUMO levels, the energy band gaps and the functional group compositions of the detected flavonoids.

  16. Dietary Intake of Flavonoids and Ventilatory Function in European Adults: A GA2LEN Study

    Directory of Open Access Journals (Sweden)

    Vanessa Garcia-Larsen

    2018-01-01

    Full Text Available Background: Flavonoids exert anti-inflammatory properties and modulate oxidative stress in vitro, suggesting a protective effect on lung function, but epidemiological studies examining this association are scarce. Methods: A stratified random sample was drawn from the GA2LEN screening survey, in which 55,000 adults aged 15 to 75 answered a questionnaire on respiratory symptoms. Post-bronchodilator spirometry was obtained from 2850 subjects. Forced vital capacity (FVC, the ratio between the forced exhaled volume in 1 second (FEV1 and FVC (FEV1/FVC, FVC below lower limit of normal (FVC < LLN, and FEV1/FVC < LLN were calculated. Intake of the six main subclasses of flavonoids was estimated using the GA2LEN Food Frequency Questionnaire. Adjusted associations between outcomes and each subclass of flavonoids were examined with multivariate regressions. Simes’ procedure was used to test for multiple comparisons. Results: A total of 2599 subjects had valid lung function and dietary data. A lower prevalence of FVC < LLN (airway restriction was observed in those with higher total flavonoid (adjusted odds ratio (aOR, higher vs. lowest quintile intake 0.58; 95% Confidence Interval (CI 0.36, 0.94, and pro-anthocyanidin intakes (aOR 0.47; 95% CI 0.27, 0.81. A higher FEV1/FVC was associated with higher intakes of total flavonoids and pro-anthocyanidins (adjusted correlation coefficient (a β-coeff 0.33; 0.10, 0.57 and a β-coeff 0.44; 95% CI 0.19, 0.69, respectively. After Simes’ procedure, the statistical significance of each of these associations was attenuated but remained below 0.05, with the exception of total flavonoids and airway restriction. Conclusions: This population-based study in European adults provides cross-sectional evidence of a positive association of total flavonoid intake and pro-anthocyanidins and ventilatory function, and a negative association with spirometric restriction in European adults.

  17. Chemical, Bioactive, and Antioxidant Potential of Twenty Wild Culinary Mushroom Species

    Science.gov (United States)

    Sharma, S. K.; Gautam, N.

    2015-01-01

    The chemical, bioactive, and antioxidant potential of twenty wild culinary mushroom species being consumed by the people of northern Himalayan regions has been evaluated for the first time in the present study. Nutrients analyzed include protein, crude fat, fibres, carbohydrates, and monosaccharides. Besides, preliminary study on the detection of toxic compounds was done on these species. Bioactive compounds evaluated are fatty acids, amino acids, tocopherol content, carotenoids (β-carotene, lycopene), flavonoids, ascorbic acid, and anthocyanidins. Fruitbodies extract of all the species was tested for different types of antioxidant assays. Although differences were observed in the net values of individual species all the species were found to be rich in protein, and carbohydrates and low in fat. Glucose was found to be the major monosaccharide. Predominance of UFA (65–70%) over SFA (30–35%) was observed in all the species with considerable amounts of other bioactive compounds. All the species showed higher effectiveness for antioxidant capacities. PMID:26199938

  18. Chemical, Bioactive, and Antioxidant Potential of Twenty Wild Culinary Mushroom Species

    Directory of Open Access Journals (Sweden)

    S. K. Sharma

    2015-01-01

    Full Text Available The chemical, bioactive, and antioxidant potential of twenty wild culinary mushroom species being consumed by the people of northern Himalayan regions has been evaluated for the first time in the present study. Nutrients analyzed include protein, crude fat, fibres, carbohydrates, and monosaccharides. Besides, preliminary study on the detection of toxic compounds was done on these species. Bioactive compounds evaluated are fatty acids, amino acids, tocopherol content, carotenoids (β-carotene, lycopene, flavonoids, ascorbic acid, and anthocyanidins. Fruitbodies extract of all the species was tested for different types of antioxidant assays. Although differences were observed in the net values of individual species all the species were found to be rich in protein, and carbohydrates and low in fat. Glucose was found to be the major monosaccharide. Predominance of UFA (65–70% over SFA (30–35% was observed in all the species with considerable amounts of other bioactive compounds. All the species showed higher effectiveness for antioxidant capacities.

  19. Chemical, Bioactive, and Antioxidant Potential of Twenty Wild Culinary Mushroom Species.

    Science.gov (United States)

    Sharma, S K; Gautam, N

    2015-01-01

    The chemical, bioactive, and antioxidant potential of twenty wild culinary mushroom species being consumed by the people of northern Himalayan regions has been evaluated for the first time in the present study. Nutrients analyzed include protein, crude fat, fibres, carbohydrates, and monosaccharides. Besides, preliminary study on the detection of toxic compounds was done on these species. Bioactive compounds evaluated are fatty acids, amino acids, tocopherol content, carotenoids (β-carotene, lycopene), flavonoids, ascorbic acid, and anthocyanidins. Fruitbodies extract of all the species was tested for different types of antioxidant assays. Although differences were observed in the net values of individual species all the species were found to be rich in protein, and carbohydrates and low in fat. Glucose was found to be the major monosaccharide. Predominance of UFA (65-70%) over SFA (30-35%) was observed in all the species with considerable amounts of other bioactive compounds. All the species showed higher effectiveness for antioxidant capacities.

  20. Vaccinium corymbosum L. (blueberry) extracts exhibit protective action against cadmium toxicity in Saccharomyces cerevisiae cells.

    Science.gov (United States)

    Oprea, Eliza; Ruta, Lavinia L; Nicolau, Ioana; Popa, Claudia V; Neagoe, Aurora D; Farcasanu, Ileana C

    2014-01-01

    Blueberries (Vaccinium corymbosum L.) are a rich source of antioxidants and their consumption is believed to contribute to food-related protection against oxidative stress. In the present study, the chemoprotective action of blueberry extracts against cadmium toxicity was investigated using a cadmium-hypersensitive strain of Saccharomyces cerevisiae. Four varieties of blueberries were used in the study, and it was found that the extracts with high content of total anthocyanidins exhibited significant protective effect against the toxicity of cadmium and H2O2. Both the blueberry extracts and pure cyanidin exhibited protective effects against cadmium in a dose-dependent manner, but without significantly interfering with the cadmium accumulation by the yeast cells. The results imply that the blueberry extracts might be a potentially valuable food supplement for individuals exposed to high cadmium. Copyright © 2013 Elsevier Ltd. All rights reserved.

  1. The Influence of Different Air-Drying Conditions on Bioactive Compounds and Antioxidant Activity of Berries.

    Science.gov (United States)

    Bustos, Mariela C; Rocha-Parra, Diego; Sampedro, Ines; de Pascual-Teresa, Sonia; León, Alberto E

    2018-03-21

    The aim of the present research was to study the effect of convective drying on color, bioactive compounds, and antioxidant activity of berry fruits and to chemically characterize the polyphenolic composition of raspberry, boysenberry, redcurrants, and blackcurrants fruit. Drying berries at 65 °C provoked the best conservations of color, particularly for boysenberry and blackcurrant. Drying at 65 °C was also the condition that showed higher level of polyphenols, while drying at 50 or 130 °C showed above % degradation of them due to the long time or high temperature drying. Radical scavenging activity was the predominant antioxidant mechanism in all samples, with 65 °C dried berries being the most active ones possibly because of polyphenol depolymerization. The anthocyanin profile showed that delphinidin and cyanidin derivatives were the most abundant anthocyanidins with different predominance between berry genera. Degradation of anthocyanins was increased with drying temperature been Cy 3-glucoside and Cy 3-rutinoside the most abundant.

  2. Affinity and selectivity of plant proteins for red wine components relevant to color and aroma traits.

    Science.gov (United States)

    Granato, Tiziana Mariarita; Ferranti, Pasquale; Iametti, Stefania; Bonomi, Francesco

    2018-08-01

    The effects of fining with various plant proteins were assessed on Aglianico red wine, using both the young wine and wine aged for twelve and twenty-four months, and including wine unfined or fined with gelatin as controls. Color traits and fining efficiency were considered, along with the content of various types of phenolics and of aroma-related compounds of either varietal or fermentative origin. All agents had comparable fining efficiency, although with distinct kinetics, and had similar effects on wine color. Individual plant proteins and enzymatic hydrolyzates differed in their ability to interact with some anthocyanins, with specific proanthocyanidins complexes, and with some aroma components of fermentative origin. Changes in varietal aroma components upon fining were very limited or absent. Effects of all the fining agents tested in this study on the anthocyanidin components were most noticeable in young red wine, and decreased markedly with increasing wine ageing. Copyright © 2018 Elsevier Ltd. All rights reserved.

  3. Characterization of phenolic and other polar compounds in peel and flesh of pink guava (Psidium guajava L. cv. 'Criolla') by ultra-high performance liquid chromatography with diode array and mass spectrometric detection.

    Science.gov (United States)

    Rojas-Garbanzo, Carolina; Zimmermann, Benno F; Schulze-Kaysers, Nadine; Schieber, Andreas

    2017-10-01

    Pink guava (Psidium guajava L.) is a highly consumed fruit in tropical countries. Despite of interesting research on health effects of this fruit, investigations into the profile of secondary plant metabolites are scarce. In this study, the phenolic compounds in the peel and flesh of pink guava were characterized by ultra-high performance liquid chromatography with diode array and mass spectrometric detection. Sixty phenolic compounds were characterized by MS 2 and classified as ellagitannins, flavones, flavonols, flavanols, proanthocyanidins, dihydrochalcones, and anthocyanidins, and non-flavonoids such as phenolic acid derivatives, stilbenes, acetophenones, and benzophenones. Forty-two polyphenols are reported for the first time in both peel and flesh, and twenty-four compounds were detected for the first time in P. guajava, e.g., phlorizin, nothofagin, astringin, chrysin-C-glucoside, valoneic acid bilactone, cinnamoyl-glucoside, and two dimethoxycinnamoyl-hexosides. Copyright © 2016 Elsevier Ltd. All rights reserved.

  4. Tentative identification of polyphenols in Sempervivum tectorum and assessment of the antimicrobial activity of Sempervivum L.

    Science.gov (United States)

    Abram, V; Donko, M

    1999-02-01

    Polyphenols were isolated from sliced fresh leaves of Sempervivum tectorum. After 21 h of extraction by methanol and removal of chlorophyll, ethyl acetate was used to separate oligomeric and polymeric polyphenols: 0.07% of oligomeric and 0.13% of polymeric polyphenols were found. After acidic hydrolysis of the oligomeric polyphenols, it was established by TLC, HPLC, and FAB mass spectra that kaempferol was the unique aglycon of the three main oligomeric constituents of S. tectorum. Paper chromatography suggested delphinidol to be the only anthocyanidin detectable in the material obtained by acidic hydrolysis of the polymeric polyphenol fraction. After Haslam degradation of the same polymeric polyphenol fraction, only 4-thiobenzyl-(-)-epigallocatechin and 4-thiobenzyl-(-)-epigallocatechin-3-gallate were found and tentatively identified. We concluded that procyanidins of B2 type could be the major components of the polymeric polyphenol fraction of this plant. Antimicrobial activity of Sempervivum L. leaves against six of seven selected microorganisms was observed.

  5. Crystal Structures of Glycosyltransferase UGT78G1 Reveal the Molecular Basis for Glycosylation and Deglycosylation of (Iso)flavonoids

    Energy Technology Data Exchange (ETDEWEB)

    Modolo, Luzia V.; Li, Lenong; Pan, Haiyun; Blount, Jack W.; Dixon, Richard A.; Wang, Xiaoqiang; (SRNF)

    2010-09-21

    The glycosyltransferase UGT78G1 from Medicago truncatula catalyzes the glycosylation of various (iso)flavonoids such as the flavonols kaempferol and myricetin, the isoflavone formononetin, and the anthocyanidins pelargonidin and cyanidin. It also catalyzes a reverse reaction to remove the sugar moiety from glycosides. The structures of UGT78G1 bound with uridine diphosphate or with both uridine diphosphate and myricetin were determined at 2.1 {angstrom} resolution, revealing detailed interactions between the enzyme and substrates/products and suggesting a distinct binding mode for the acceptor/product. Comparative structural analysis and mutagenesis identify glutamate 192 as a key amino acid for the reverse reaction. This information provides a basis for enzyme engineering to manipulate substrate specificity and to design effective biocatalysts with glycosylation and/or deglycosylation activity.

  6. Measurement of food flavonoids by high-performance liquid chromatography: A review.

    Science.gov (United States)

    Merken, H M; Beecher, G R

    2000-03-01

    The flavonoids are plant polyphenols found frequently in fruits, vegetables, and grains. Divided into several subclasses, they include the anthocyanidins, pigments chiefly responsible for the red and blue colors in fruits, fruit juices, wines, and flowers; the catechins, concentrated in tea; the flavanones and flavanone glycosides, found in citrus and honey; and the flavones, flavonols, and flavonol glycosides, found in tea, fruits, vegetables, and honey. Known for their hydrogen-donating antioxidant activity as well as their ability to complex divalent transition metal cations, flavonoids are propitious to human health. Computer-controlled high-performance liquid chromatography (HPLC) has become the analytical method of choice. Many systems have been developed for the detection and quantification of flavonoids across one, two, or three subclasses. A summary of the various HPLC and sample preparation methods that have been employed to quantify individual flavonoids within a subclass or across several subclasses are tabulated in this review.

  7. Regulation of anthocyanin and proanthocyanidin biosynthesis by Medicago truncatula bHLH transcription factor MtTT8.

    Science.gov (United States)

    Li, Penghui; Chen, Beibei; Zhang, Gaoyang; Chen, Longxiang; Dong, Qiang; Wen, Jiangqi; Mysore, Kirankumar S; Zhao, Jian

    2016-05-01

    The MYB- basic helix-loop-helix (bHLH)-WD40 complexes regulating anthocyanin and proanthocyanidin (PA) biosynthesis in plants are not fully understood. Here Medicago truncatula bHLH MtTT8 was characterized as a central component of these ternary complexes that control anthocyanin and PA biosynthesis. Mttt8 mutant seeds have a transparent testa phenotype with reduced PAs and anthocyanins. MtTT8 restores PA and anthocyanin productions in Arabidopsis tt8 mutant. Ectopic expression of MtTT8 restores anthocyanins and PAs in mttt8 plant and hairy roots and further enhances both productions in wild-type hairy roots. Transcriptomic analyses and metabolite profiling of mttt8 mutant seeds and M. truncatula hairy roots (mttt8 mutant, mttt8 mutant complemented with MtTT8, or MtTT8 overexpression lines) indicate that MtTT8 regulates a subset of genes involved in PA and anthocyanin biosynthesis. MtTT8 is genetically regulated by MtLAP1, MtPAR and MtWD40-1. Combinations of MtPAR, MtLAP1, MtTT8 and MtWD40-1 activate MtTT8 promoter in yeast assay. MtTT8 interacts with these transcription factors to form regulatory complexes. MtTT8, MtWD40-1 and an MYB factor, MtPAR or MtLAP1, interacted and activated promoters of anthocyanidin reductase and anthocyanidin synthase to regulate PA and anthocyanin biosynthesis, respectively. Our results provide new insights into the complex regulation of PA and anthocyanin biosynthesis in M. truncatula. © 2016 The Authors. New Phytologist © 2016 New Phytologist Trust.

  8. A wild 'albino' bilberry (Vaccinium myrtillus L. from Slovenia shows three bottlenecks in the anthocyanin pathway and significant differences in the expression of several regulatory genes compared to the common blue berry type.

    Directory of Open Access Journals (Sweden)

    Zala Zorenc

    Full Text Available Relative expressions of structural genes and a number of transcription factors of the anthocyanin pathway relevant in Vaccinium species, and related key enzyme activities were compared with the composition and content of metabolites in skins of ripe fruits of wild albino and blue bilberry (Vaccinium myrtillus found in Slovenia. Compared to the common blue type, the albino variant had a 151-fold lower total anthocyanin and a 7-fold lower total phenolic content in their berry skin, which correlated with lower gene expression of flavonoid 3-O-glycosyltransferase (FGT; 33-fold, flavanone 3-hydroxylase (FHT; 18-fold, anthocyanidin synthase (ANS; 11-fold, chalcone synthase (CHS, 7.6-fold and MYBPA1 transcription factor (22-fold. The expression of chalcone isomerase (CHI, dihydroflavonol 4-reductase (DFR, leucoanthocyanidin reductase (LAR, anthocyanidin reductase (ANR and MYBC2 transcription factor was reduced only by a factor of 1.5-2 in the albino berry skins, while MYBR3 and flavonoid 3',5'-hydroxylase (F3'5'H were increased to a similar extent. Expression of the SQUAMOSA class transcription factor TDR4, in contrast, was independent of the color type and does therefore not seem to be correlated with anthocyanin formation in this variant. At the level of enzymes, significantly lower FHT and DFR activities, but not of phenylalanine ammonia-lyase (PAL and CHS/CHI, were observed in the fruit skins of albino bilberries. A strong increase in relative hydroxycinnamic acid derivative concentrations indicates the presence of an additional bottleneck in the general phenylpropanoid pathway at a so far unknown step between PAL and CHS.

  9. De novo Assembly of the Camellia nitidissima Transcriptome Reveals Key Genes of Flower Pigment Biosynthesis

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    Xingwen Zhou

    2017-09-01

    Full Text Available The golden camellia, Camellia nitidissima Chi., is a well-known ornamental plant that is known as “the queen of camellias” because of its golden yellow flowers. The principal pigments in the flowers are carotenoids and flavonol glycosides. Understanding the biosynthesis of the golden color and its regulation is important in camellia breeding. To obtain a comprehensive understanding of flower development in C. nitidissima, a number of cDNA libraries were independently constructed during flower development. Using the Illumina Hiseq2500 platform, approximately 71.8 million raw reads (about 10.8 gigabase pairs were obtained and assembled into 583,194 transcripts and 466, 594 unigenes. A differentially expressed genes (DEGs and co-expression network was constructed to identify unigenes correlated with flower color. The analysis of DEGs and co-expressed network involved in the carotenoid pathway indicated that the biosynthesis of carotenoids is regulated mainly at the transcript level and that phytoene synthase (PSY, β -carotene 3-hydroxylase (CrtZ, and capsanthin synthase (CCS1 exert synergistic effects in carotenoid biosynthesis. The analysis of DEGs and co-expressed network involved in the flavonoid pathway indicated that chalcone synthase (CHS, naringenin 3-dioxygenase (F3H, leucoanthocyanidin dioxygenase(ANS, and flavonol synthase (FLS play critical roles in regulating the formation of flavonols and anthocyanidin. Based on the gene expression analysis of the carotenoid and flavonoid pathways, and determinations of the pigments, we speculate that the high expression of PSY and CrtZ ensures the production of adequate levels of carotenoids, while the expression of CHS, FLS ensures the production of flavonols. The golden yellow color is then the result of the accumulation of carotenoids and flavonol glucosides in the petals. This study of the mechanism of color formation in golden camellia points the way to breeding strategies that exploit gene

  10. Flavonoid intake and cardiovascular disease mortality: a prospective study in postmenopausal women.

    Science.gov (United States)

    Mink, Pamela J; Scrafford, Carolyn G; Barraj, Leila M; Harnack, Lisa; Hong, Ching-Ping; Nettleton, Jennifer A; Jacobs, David R

    2007-03-01

    Dietary flavonoids may have beneficial cardiovascular effects in human populations, but epidemiologic study results have not been conclusive. We used flavonoid food composition data from 3 recently available US Department of Agriculture databases to improve estimates of dietary flavonoid intake and to evaluate the association between flavonoid intake and cardiovascular disease (CVD) mortality. Study participants were 34 489 postmenopausal women in the Iowa Women's Health Study who were free of CVD and had complete food-frequency questionnaire information at baseline. Intakes of total flavonoids and 7 subclasses were categorized into quintiles, and food sources were grouped into frequency categories. Proportional hazards rate ratios (RR) were computed for CVD, coronary heart disease (CHD), stroke, and total mortality after 16 y of follow-up. After multivariate adjustment, significant inverse associations were observed between anthocyanidins and CHD, CVD, and total mortality [RR (95% CI) for any versus no intake: 0.88 (0.78, 0.99), 0.91 (0.83, 0.99), and 0.90 (0.86, 0.95)]; between flavanones and CHD [RR for highest quintile versus lowest: 0.78 (0.65, 0.94)]; and between flavones and total mortality [RR for highest quintile versus lowest: 0.88 (0.82, 0.96)]. No association was found between flavonoid intake and stroke mortality. Individual flavonoid-rich foods associated with significant mortality reduction included bran (added to foods; associated with stroke and CVD); apples or pears or both and red wine (associated with CHD and CVD); grapefruit (associated with CHD); strawberries (associated with CVD); and chocolate (associated with CVD). Dietary intakes of flavanones, anthocyanidins, and certain foods rich in flavonoids were associated with reduced risk of death due to CHD, CVD, and all causes.

  11. SEEDSTICK is a master regulator of development and metabolism in the Arabidopsis seed coat.

    Directory of Open Access Journals (Sweden)

    Chiara Mizzotti

    2014-12-01

    Full Text Available The role of secondary metabolites in the determination of cell identity has been an area of particular interest over recent years, and studies strongly indicate a connection between cell fate and the regulation of enzymes involved in secondary metabolism. In Arabidopsis thaliana, the maternally derived seed coat plays pivotal roles in both the protection of the developing embryo and the first steps of germination. In this regard, a characteristic feature of seed coat development is the accumulation of proanthocyanidins (PAs - a class of phenylpropanoid metabolites in the innermost layer of the seed coat. Our genome-wide transcriptomic analysis suggests that the ovule identity factor SEEDSTICK (STK is involved in the regulation of several metabolic processes, providing a strong basis for a connection between cell fate determination, development and metabolism. Using phenotypic, genetic, biochemical and transcriptomic approaches, we have focused specifically on the role of STK in PA biosynthesis. Our results indicate that STK exerts its effect by direct regulation of the gene encoding BANYULS/ANTHOCYANIDIN REDUCTASE (BAN/ANR, which converts anthocyanidins into their corresponding 2,3-cis-flavan-3-ols. Our study also demonstrates that the levels of H3K9ac chromatin modification directly correlate with the active state of BAN in an STK-dependent way. This is consistent with the idea that MADS-domain proteins control the expression of their target genes through the modification of chromatin states. STK might thus recruit or regulate histone modifying factors to control their activity. In addition, we show that STK is able to regulate other BAN regulators. Our study demonstrates for the first time how a floral homeotic gene controls tissue identity through the regulation of a wide range of processes including the accumulation of secondary metabolites.

  12. Flower colour and cytochromes P450.

    Science.gov (United States)

    Tanaka, Yoshikazu; Brugliera, Filippa

    2013-02-19

    Cytochromes P450 play important roles in biosynthesis of flavonoids and their coloured class of compounds, anthocyanins, both of which are major floral pigments. The number of hydroxyl groups on the B-ring of anthocyanidins (the chromophores and precursors of anthocyanins) impact the anthocyanin colour, the more the bluer. The hydroxylation pattern is determined by two cytochromes P450, flavonoid 3'-hydroxylase (F3'H) and flavonoid 3',5'-hydroxylase (F3'5'H) and thus they play a crucial role in the determination of flower colour. F3'H and F3'5'H mostly belong to CYP75B and CYP75A, respectively, except for the F3'5'Hs in Compositae that were derived from gene duplication of CYP75B and neofunctionalization. Roses and carnations lack blue/violet flower colours owing to the deficiency of F3'5'H and therefore lack the B-ring-trihydroxylated anthocyanins based upon delphinidin. Successful redirection of the anthocyanin biosynthesis pathway to delphinidin was achieved by expressing F3'5'H coding regions resulting in carnations and roses with novel blue hues that have been commercialized. Suppression of F3'5'H and F3'H in delphinidin-producing plants reduced the number of hydroxyl groups on the anthocyanidin B-ring resulting in the production of monohydroxylated anthocyanins based on pelargonidin with a shift in flower colour to orange/red. Pelargonidin biosynthesis is enhanced by additional expression of a dihydroflavonol 4-reductase that can use the monohydroxylated dihydrokaempferol (the pelargonidin precursor). Flavone synthase II (FNSII)-catalysing flavone biosynthesis from flavanones is also a P450 (CYP93B) and contributes to flower colour, because flavones act as co-pigments to anthocyanins and can cause blueing and darkening of colour. However, transgenic plants expression of a FNSII gene yielded paler flowers owing to a reduction of anthocyanins because flavanones are precursors of anthocyanins and flavones.

  13. Distribution and biosynthesis of flavan-3-ols in Camellia sinensis seedlings and expression of genes encoding biosynthetic enzymes.

    Science.gov (United States)

    Ashihara, Hiroshi; Deng, Wei-Wei; Mullen, William; Crozier, Alan

    2010-04-01

    The distribution of phenolic compounds in young and developing leaves, stems, main and lateral roots and cotyledons of 8-week-old tea (Camellia sinensis) seedlings was investigated using HPLC-MS(2). Fourteen compounds, flavan-3-ols, chlorogenic acids, and kaempferol-O-glycosides, were identified on the basis of their retention time, absorbance spectrum, and MS fragmentation pattern. The major phenolics were (-)-epigallocatechin-3-O-gallate and (-)-epicatechin-3-O-gallate, located principally in the green parts of the seedlings. Considerable amounts of radioactivity from [ring-(14)C]phenylalanine were incorporated in (-)-epicatechin, (-)-epigallocatechin, (-)-epicatechin-3-O-gallate and (-)-epigallocatechin-3-O-gallate, by tissues of young and developing leaves and stems. Expression of genes encoding enzymes involved in flavan-3-ol biosynthesis, CHS, CHI, F3H, F3'5'H, DFR, ANS, ANR and LAR was investigated. Transcripts of all genes, except LAR, were more abundant in leaves and stems than in roots and cotyledons. No significant difference was found in the amount of transcript of LAR. These findings indicate that in tea seedlings flavan-3-ols are produced by a naringenin-chalcone-->naringenin-->dihydrokaempferol pathway. Dihydrokaempferol is a branch point in the synthesis of (-)-epigallocatechin-3-O-gallate and other flavan-3-ols which can be formed by routes beginning with either a flavonoid 3'-hydroxylase mediated conversion of the flavonol to dihydroquercetin or a flavonoid 3',5'-hydroxylase-catalysed conversion to dihydromyricetin with subsequent steps involving sequential reactions catalysed by dihydroflavanol 4-reductase, anthocyanidin synthase, anthocyanidin reductase and flavan-3-ol gallate synthase. Copyright 2010 Elsevier Ltd. All rights reserved.

  14. Metabolic and molecular analyses of white mutant Vaccinium berries show down-regulation of MYBPA1-type R2R3 MYB regulatory factor.

    Science.gov (United States)

    Primetta, Anja K; Karppinen, Katja; Riihinen, Kaisu R; Jaakola, Laura

    2015-09-01

    MYBPA1-type R2R3 MYB transcription factor shows down-regulation in white mutant berries of Vaccinium uliginosum deficient in anthocyanins but not proanthocyanidins suggesting a role in the regulation of anthocyanin biosynthesis. Berries of the genus Vaccinium are among the best natural sources of flavonoids. In this study, the expression of structural and regulatory flavonoid biosynthetic genes and the accumulation of flavonoids in white mutant and blue-colored wild-type bog bilberry (V. uliginosum) fruits were measured at different stages of berry development. In contrast to high contents of anthocyanins in ripe blue-colored berries, only traces were detected by HPLC-ESI-MS in ripe white mutant berries. However, similar profile and high levels of flavonol glycosides and proanthocyanidins were quantified in both ripe white and ripe wild-type berries. Analysis with qRT-PCR showed strong down-regulation of structural genes chalcone synthase (VuCHS), dihydroflavonol 4-reductase (VuDFR) and anthocyanidin synthase (VuANS) as well as MYBPA1-type transcription factor VuMYBPA1 in white berries during ripening compared to wild-type berries. The profiles of transcript accumulation of chalcone isomerase (VuCHI), anthocyanidin reductase (VuANR), leucoanthocyanidin reductase (VuLAR) and flavonoid 3'5' hydroxylase (VuF3'5'H) were more similar between the white and the wild-type berries during fruit development, while expression of UDP-glucose: flavonoid 3-O-glucosyltransferase (VuUFGT) showed similar trend but fourfold lower level in white mutant. VuMYBPA1, the R2R3 MYB family member, is a homologue of VmMYB2 of V. myrtillus and VcMYBPA1 of V. corymbosum and belongs to MYBPA1-type MYB family which members are shown in some species to be related with proanthocyanidin biosynthesis in fruits. Our results combined with earlier data of the role of VmMYB2 in white mutant berries of V. myrtillus suggest that the regulation of anthocyanin biosynthesis in Vaccinium species could differ

  15. Activation tagging in tomato identifies a transcriptional regulator of anthocyanin biosynthesis, modification, and transport.

    Science.gov (United States)

    Mathews, Helena; Clendennen, Stephanie K; Caldwell, Colby G; Liu, Xing Liang; Connors, Karin; Matheis, Nikolaus; Schuster, Debra K; Menasco, D J; Wagoner, Wendy; Lightner, Jonathan; Wagner, D Ry

    2003-08-01

    We have developed a high-throughput T-DNA insertional mutagenesis program in tomato using activation tagging to identify genes that regulate metabolic pathways. One of the activation-tagged insertion lines (ant1) showed intense purple pigmentation from the very early stage of shoot formation in culture, reflecting activation of the biosynthetic pathway leading to anthocyanin accumulation. The purple coloration resulted from the overexpression of a gene that encodes a MYB transcription factor. Vegetative tissues of ant1 plants displayed intense purple color, and the fruit showed purple spotting on the epidermis and pericarp. The gene-to-trait relationship of ant1 was confirmed by the overexpression of ANT1 in transgenic tomato and in tobacco under the control of a constitutive promoter. Suppression subtractive hybridization and RNA hybridization analysis of the purple tomato plants indicated that the overexpression of ANT1 caused the upregulation of genes that encode proteins in both the early and later steps of anthocyanidin biosynthesis as well as genes involved in the glycosylation and transport of anthocyanins into the vacuole.

  16. Biochemical and functional characterization of AcUFGT3a, a galactosyltransferase involved in anthocyanin biosynthesis in the red-fleshed kiwifruit (Actinidia chinensis).

    Science.gov (United States)

    Liu, Yanfei; Zhou, Bin; Qi, Yingwei; Liu, Cuihua; Liu, Zhande; Ren, Xiaolin

    2018-04-01

    Much of the diversity of anthocyanin pigmentation in plant tissues is due to the action of glycosyltransferases, which attach sugar moieties to the anthocyanin aglycone. This step can increase both their solubility and stability. We investigated the pigmentation of the outer and inner pericarps of developing fruits of the red-fleshed kiwifruit Actinidia chinensis cv. 'Hongyang'. The results show that the red color of the inner pericarp is due to anthocyanin. Based on expression analyses of structural genes, AcUFGT was shown to be the key gene involved in the anthocyanin biosynthetic pathway. Expression of AcUFGT in developing fruit paralleled changes in anthocyanin concentration. Thirteen putative UFGT genes, including different transcripts, were identified in the genome of 'Hongyang'. Among these, only the expression of AcUFGT3a was found to be highly consistent with anthocyanin accumulation. Fruit infiltrated with virus-induced gene silencing showed delayed red colorations, lower anthocyanin contents and lower expressions of AcUFGT3a. At the same time, transient overexpression of AcUFGT3a in both Actinidia arguta and green apple fruit resulted in higher anthocyanin contents and deeper red coloration. In vitro biochemical assays revealed that recombinant AcUFGT3a recognized only anthocyanidins as substrate but not flavonols. Also, UDP-galactose was used preferentially as the sugar donor. These results indicate AcUFGT3a is the key enzyme regulating anthocyanin accumulation in red-fleshed kiwifruit. © 2017 Scandinavian Plant Physiology Society.

  17. Caffeoylquinic acid-rich purple sweet potato extract, with or without anthocyanin, imparts neuroprotection and contributes to the improvement of spatial learning and memory of SAMP8 mouse.

    Science.gov (United States)

    Sasaki, Kazunori; Han, Junkyu; Shimozono, Hidetoshi; Villareal, Myra O; Isoda, Hiroko

    2013-05-29

    The effects of caffeoylquinic acid (CQA)-rich purple sweet potato (PSP) extract, with (PSPEa) or without (PSPEb) anthocyanin, on the improvement of spatial learning and memory of senescence-accelerated prone mouse strain (SAMP) 8 was determined. SAMP8 was treated with 20 mg/kg/day of PSPEa or PSPEb for 30 days. The effect on spatial learning and memory and the molecular mechanism of this effect were determined in vivo (SAMP8) and in vitro (SH-SY5Y cells). PSPEa or PSPEb reduced the escape latency time of SAMP8 by 17.0 ± 8.0 and 14.2 ± 5.8 s (P overexpression of antioxidant-, energy metabolism-, and neuronal plasticity-related proteins in the brain of SAMP8. Additionally, PSPEa and PSPEb increased the cell viability by 141.6 and 133% as compared to Aβ1-42-treated cells. These findings suggest that PSP rich in CQA derivatives with or without anthocyanidine had a neuroprotective effect on mouse brain and can improve the spatial learning and memory of SAMP8.

  18. The Transcriptional Repressor MYB2 Regulates Both Spatial and Temporal Patterns of Proanthocyandin and Anthocyanin Pigmentation in Medicago truncatula[OPEN

    Science.gov (United States)

    2015-01-01

    Accumulation of anthocyanins and proanthocyanidins (PAs) is limited to specific cell types and developmental stages, but little is known about how antagonistically acting transcriptional regulators work together to determine temporal and spatial patterning of pigmentation at the cellular level, especially for PAs. Here, we characterize MYB2, a transcriptional repressor regulating both anthocyanin and PA biosynthesis in the model legume Medicago truncatula. MYB2 was strongly upregulated by MYB5, a major regulator of PA biosynthesis in M. truncatula and a component of MYB-basic helix loop helix-WD40 (MBW) activator complexes. Overexpression of MYB2 abolished anthocyanin and PA accumulation in M. truncatula hairy roots and Arabidopsis thaliana seeds, respectively. Anthocyanin deposition was expanded in myb2 mutant seedlings and flowers accompanied by increased anthocyanin content. PA mainly accumulated in the epidermal layer derived from the outer integument in the M. truncatula seed coat, starting from the hilum area. The area of PA accumulation and ANTHOCYANIDIN REDUCTASE expression was expanded into the seed body at the early stage of seed development in the myb2 mutant. Genetic, biochemical, and cell biological evidence suggests that MYB2 functions as part of a multidimensional regulatory network to define the temporal and spatial pattern of anthocyanin and PA accumulation linked to developmental processes. PMID:26410301

  19. The Transcriptional Repressor MYB2 Regulates Both Spatial and Temporal Patterns of Proanthocyandin and Anthocyanin Pigmentation in Medicago truncatula.

    Science.gov (United States)

    Jun, Ji Hyung; Liu, Chenggang; Xiao, Xirong; Dixon, Richard A

    2015-10-01

    Accumulation of anthocyanins and proanthocyanidins (PAs) is limited to specific cell types and developmental stages, but little is known about how antagonistically acting transcriptional regulators work together to determine temporal and spatial patterning of pigmentation at the cellular level, especially for PAs. Here, we characterize MYB2, a transcriptional repressor regulating both anthocyanin and PA biosynthesis in the model legume Medicago truncatula. MYB2 was strongly upregulated by MYB5, a major regulator of PA biosynthesis in M. truncatula and a component of MYB-basic helix loop helix-WD40 (MBW) activator complexes. Overexpression of MYB2 abolished anthocyanin and PA accumulation in M. truncatula hairy roots and Arabidopsis thaliana seeds, respectively. Anthocyanin deposition was expanded in myb2 mutant seedlings and flowers accompanied by increased anthocyanin content. PA mainly accumulated in the epidermal layer derived from the outer integument in the M. truncatula seed coat, starting from the hilum area. The area of PA accumulation and ANTHOCYANIDIN REDUCTASE expression was expanded into the seed body at the early stage of seed development in the myb2 mutant. Genetic, biochemical, and cell biological evidence suggests that MYB2 functions as part of a multidimensional regulatory network to define the temporal and spatial pattern of anthocyanin and PA accumulation linked to developmental processes. © 2015 American Society of Plant Biologists. All rights reserved.

  20. New insights into the medicinal importance, physiological functions and bioanalytical aspects of an important bioactive compound of foods ‘Hyperin’: Health benefits of the past, the present, the future

    Directory of Open Access Journals (Sweden)

    Kanika Patel

    2018-03-01

    Full Text Available Herbal medicines have been used for the treatment of various disorders in the world since very early age. A large number of phytochemicals have been derived from the natural sources in the form of food supplement, neutraceuticals, oils and colour pigments. Flavonoids are a widely distributed group of phytochemicals having benzo-pyrone nucleus. Till so far more than 4000 different types of flavonoids have been described and categorized into different groups like flavonols, flavones, flavanones, isoflavones, catechins and anthocyanidins. Flavonoids have an attractive candidate in the food industry as natural colorants due to its health beneficial effect and safety issue. Hyperin, an important flvonoid were found in the different plants have various pharmacological activities like antioxidant, anti-inflammatory, anticancer, antiviral, antibacterial, antiparasitic, cardioprotective, hepatoprotective and antispasmodic. The aim of this review is to collect all the valuable scientific information of hyperin regarding its medicinal importance, pharmacological activities, isolation and analytical techniques. From the presented data’s in this review it will be beneficial to the scientific person, pharmaceutical manufacturer and consumers in order to it health beneficial effect of hyperin. Thus this valuable information will be helpful to the researchers for developing alternative methods of treatment for different diseases.

  1. Functional analysis of Antirrhinum kelloggii flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase genes; critical role in flower color and evolution in the genus Antirrhinum.

    Science.gov (United States)

    Ishiguro, Kanako; Taniguchi, Masumi; Tanaka, Yoshikazu

    2012-05-01

    The enzymes flavonoid 3'-hydroxylase (F3'H) and flavonoid 3',5'-hydroxylase (F3'5'H) play an important role in flower color by determining the B-ring hydroxylation pattern of anthocyanins, the major floral pigments. F3'5'H is necessary for biosynthesis of the delphinidin-based anthocyanins that confer a violet or blue color to most plants. Antirrhinum majus does not produce delphinidin and lacks violet flower colour while A. kelloggii produces violet flowers containing delphinidin. To understand the cause of this inter-specific difference in the Antirrhinum genus, we isolated one F3'H and two F3'5'H homologues from the A. kelloggii petal cDNA library. Their amino acid sequences showed high identities to F3'Hs and F3'5'Hs of closely related species. Transgenic petunia expressing these genes had elevated amounts of cyanidin and delphinidin respectively, and flower color changes in the transgenics reflected the type of accumulated anthocyanidins. The results indicate that the homologs encode F3'H and F3'5'H, respectively, and that the ancestor of A. majus lost F3'5'H activity after its speciation from the ancestor of A. kelloggii.

  2. Comparative study of anthocyanin composition, antimicrobial and antioxidant activity in bilberry (Vaccinium myrtillus L.) and blueberry (Vaccinium corymbosum L.) fruits.

    Science.gov (United States)

    Burdulis, Deividas; Sarkinas, Antanas; Jasutiené, Ina; Stackevicené, Elicija; Nikolajevas, Laurynas; Janulis, Valdimaras

    2009-01-01

    Simultaneous comparison of bilberry (Vaccinium myrtillus L.) and blueberry (Vaccinium corymbosum L) fruits for their anthocyanin composition, antimicrobial and antioxidant activity is reported. The aim of this study was to investigate and to compare anthocyanin composition, antimicrobial and antioxidant activity in bilberry and blueberry fruits and their skins. The investigations revealed that the highest amount of total anthocyanins was observed in fruits skins of blueberry cultivars. The results, obtained by chromatographic analysis, indicated that cyanidin is a dominant anthocyanidin in bilberry and malvidin in blueberry samples. Extracts of "Herbert", "Coville", "Toro" blueberry cultivars and bilberry fruits revealed antimicrobial properties. Citrobacter freundii (ATCC 8090) and Enterococcus faecalis (ATCC29212) were the most sensitive among eight tested Gram-negative and Gram-positive bacteria. Significant differences between berry and skin extracts were not established. Studies with fruits showed that the strongest antioxidant activity possesses blueberry cultivar "Berkeley" (82.13 +/- 0.51%). Meanwhile, the amount of quenched free radicals in bilberry samples was 63.72 +/- 1.11%, respectively. The lowest antioxidant activity was estimated in blueberry cultivar "Coville". Accordingly, the strongest antiradical properties were estimated in blueberry cultivar "Ama" fruit skins. Bilberry fruit skin samples possess strong antiradical activity as well (82.69 +/- 0.37%).

  3. Methyl jasmonate affects phenolic metabolism and gene expression in blueberry (Vaccinium corymbosum).

    Science.gov (United States)

    Cocetta, Giacomo; Rossoni, Mara; Gardana, Claudio; Mignani, Ilaria; Ferrante, Antonio; Spinardi, Anna

    2015-02-01

    Blueberry (Vaccinium corymbosum) is a fruit very much appreciated by consumers for its antioxidant potential and health-promoting traits. Its beneficial potential properties are mainly due to a high content of anthocyanins and their amount can change after elicitation with methyl jasmonate. The aim of this work is to evaluate the changes in expression of several genes, accumulation of phenolic compounds and alterations in antioxidant potential in two different blueberry cultivars ('Duke' and 'Blueray') in response to methyl jasmonate (0.1 mM). Results showed that 9 h after treatment, the expression of phenylalanine ammonium lyase, chalcone synthase and anthocyanidin synthase genes was stimulated more in the 'Blueray' variety. Among the phenols measured an increase was recorded also for epicatechin and anthocyanin concentrations. 'Duke' is a richer sourche of anthocyanins compared to 'Blueray', treatment with methyl jasmonate promoted in 'Blueray' an increase in pigments as well as in the antioxidant potential, especially in fully ripe berries, but treated 'Duke' berries had greater levels, which were not induced by methyl jasmonate treatment. In conclusion, methyl jasmonate was, in some cases, an effective elicitor of phenolic metabolism and gene expression in blueberry, though with different intensity between cultivars. © 2014 Scandinavian Plant Physiology Society.

  4. Liquid chromatographic/electrospray ionization quadrupole/time of flight tandem mass spectrometric study of polyphenolic composition of different Vaccinium berry species and their comparative evaluation.

    Science.gov (United States)

    Ancillotti, Claudia; Ciofi, Lorenzo; Rossini, Daniele; Chiuminatto, Ugo; Stahl-Zeng, Jianru; Orlandini, Serena; Furlanetto, Sandra; Del Bubba, Massimo

    2017-02-01

    Ultra-high-performance liquid chromatography coupled with high-resolution quadrupole-time of flight mass spectrometry with both negative and positive ionization was used for comprehensively investigating the phenolic and polyphenolic compounds in berries from three spontaneous or cultivated Vaccinium species (i.e., Vaccinium myrtillus, Vaccinium uliginosum subsp. gaultherioides, and Vaccinium corymbosum). More than 200 analytes, among phenolic and polyphenolic compounds belonging to the classes of anthocyanins, monomeric and oligomeric flavonols, flavanols, dihydrochalcones, phenolic acids, together with other polyphenolic compounds of mixed structural characteristics, were identified. Some of the polyphenols herein investigated, such as anthocyanidin glucuronides and malvidin-feruloyl-hexosides in V. myrtillus, or anthocyanindin aldopentosides and coumaroyl-hexosides in V. uliginosum subsp. gaultherioides and a large number of proanthocyanidins with high molecular weight in all species, were described for the first time in these berries. Principal component analysis applied on original LC-TOF data, acquired in survey scan mode, successfully discriminated the three Vaccinium berry species investigated, on the basis of their polyphenolic composition, underlying one more time the fundamental role of mass spectrometry for food characterization.

  5. Food macromolecule based nanodelivery systems for enhancing the bioavailability of polyphenols

    Directory of Open Access Journals (Sweden)

    Bing Hu

    2017-01-01

    Full Text Available Diet polyphenols—primarily categorized into flavonoids (e.g., flavonols, flavones, flavan-3-ols, anthocyanidins, flavanones, and isoflavones and nonflavonoids (with major subclasses of stilbenes and phenolic acids—are reported to have health-promoting effects, such as antioxidant, antiinflammatory, anticarcinoma, antimicrobial, antiviral, and cardioprotective properties. However, their applications in functional foods or medicine are limited because of their inefficient systemic delivery and poor oral bioavailability. Epigallocatechin-3-gallate, curcumin, and resveratrol are the well-known representatives of the bioactive diet polyphenols but with poor bioavailability. Food macromolecule based nanoparticles have been fabricated using reassembled proteins, crosslinked polysaccharides, protein–polysaccharide conjugates (complexes, as well as emulsified lipid via safe procedures that could be applied in food. The human gastrointestinal digestion tract is the first place where the food grade macromolecule nanoparticles exert their effects on improving the bioavailability of diet polyphenols, via enhancing their solubility, preventing their degradation in the intestinal environment, elevating the permeation in small intestine, and even increasing their contents in the bloodstream. We contend that the stability and structure behaviors of nanocarriers in the gastrointestinal tract environment and the effects of nanoencapsulation on the metabolism of polyphenols warrant more focused attention in further studies.

  6. Molecular Cloning and Functional Characterization of a Dihydroflavonol 4-Reductase from Vitis bellula.

    Science.gov (United States)

    Zhu, Yue; Peng, Qingzhong; Li, Kegang; Xie, De-Yu

    2018-04-10

    Vitis bellula is a new grape crop in southern China. Berries of this species are rich in antioxidative anthocyanins and proanthocyanidins. This study reports cloning and functional characterization of a cDNA encoding a V. bellula dihydroflavonol reductase (VbDFR) involved in the biosynthesis of anthocyanins and proanthocyanidins. A cDNA including 1014 bp was cloned from young leaves and its open reading frame (ORF) was deduced encoding 337 amino acids, highly similar to V. vinifera DFR (VvDFR). Green florescence protein fusion and confocal microscopy analysis determined the cytosolic localization of VbDFR in plant cells. A soluble recombinant VbDFR was induced and purified from E. coli for enzyme assay. In the presence of NADPH, the recombinant enzyme catalyzed dihydrokaempferol (DHK) and dihydroquercetin (DHQ) to their corresponding leucoanthocyanidins. The VbDFR cDNA was introduced into tobacco plants via Agrobacterium -mediated transformation. The overexpression of VbDFR increased anthocyanin production in flowers. Anthocyanin hydrolysis and chromatographic analysis revealed that transgenic flowers produced pelargonidin and delphinidin, which were not detected in control flowers. These data demonstrated that the overexpression of VbDFR produced new tobacco anthocyanidins. In summary, all data demonstrate that VbDFR is a useful gene to provide three types of substrates for metabolic engineering of anthocyanins and proanthocyanidins in grape crops and other crops.

  7. Molecular Cloning and Functional Characterization of a Dihydroflavonol 4-Reductase from Vitis bellula

    Directory of Open Access Journals (Sweden)

    Yue Zhu

    2018-04-01

    Full Text Available Vitis bellula is a new grape crop in southern China. Berries of this species are rich in antioxidative anthocyanins and proanthocyanidins. This study reports cloning and functional characterization of a cDNA encoding a V. bellula dihydroflavonol reductase (VbDFR involved in the biosynthesis of anthocyanins and proanthocyanidins. A cDNA including 1014 bp was cloned from young leaves and its open reading frame (ORF was deduced encoding 337 amino acids, highly similar to V. vinifera DFR (VvDFR. Green florescence protein fusion and confocal microscopy analysis determined the cytosolic localization of VbDFR in plant cells. A soluble recombinant VbDFR was induced and purified from E. coli for enzyme assay. In the presence of NADPH, the recombinant enzyme catalyzed dihydrokaempferol (DHK and dihydroquercetin (DHQ to their corresponding leucoanthocyanidins. The VbDFR cDNA was introduced into tobacco plants via Agrobacterium-mediated transformation. The overexpression of VbDFR increased anthocyanin production in flowers. Anthocyanin hydrolysis and chromatographic analysis revealed that transgenic flowers produced pelargonidin and delphinidin, which were not detected in control flowers. These data demonstrated that the overexpression of VbDFR produced new tobacco anthocyanidins. In summary, all data demonstrate that VbDFR is a useful gene to provide three types of substrates for metabolic engineering of anthocyanins and proanthocyanidins in grape crops and other crops.

  8. Correlation between the potency of flavonoids for cytochrome c reduction and inhibition of cardiolipin-induced peroxidase activity.

    Science.gov (United States)

    Lagoa, Ricardo; Samhan-Arias, Alejandro K; Gutierrez-Merino, Carlos

    2017-05-06

    There are large differences between flavonoids to protect against apoptosis, a process in which cytochrome c (Cyt c) plays a key role. In this work, we show that 7 of 13 flavonoids studied have a capacity to reduce Cyt c similar or higher than ascorbate, the flavonols quercetin, kaempferol and myricetin, flavanol epigallocatechin-gallate, anthocyanidins cyanidin and malvidin, and the flavone luteolin. In contrast, the kaempferol 3(O)- and 3,4'(O)-methylated forms, the flavanone naringenin, and also apigenin and chrysin, had a negligible reducing capacity. Equilibrium dialysis and quenching of 1,6-diphenyl-1,3,5-hexatriene fluorescence experiments showed that flavonoids did not interfere with Cyt c binding to cardiolipin (CL)/phosphatidylcholine (PC) vesicles. However, the CL-induced loss of Cyt c Soret band intensity was largely attenuated by flavonoids, pointing out a stabilizing action against Cyt c unfolding in the complex. Moreover, flavonoids that behave as Cyt c reductants also inhibited the pro-apoptotic CL-induced peroxidase activity of Cyt c, indicating that modulation of Cyt c signaling are probable mechanisms behind the protective biological activities of flavonoids. © 2016 BioFactors, 43(3):451-468, 2017. © 2017 International Union of Biochemistry and Molecular Biology.

  9. Flavonoids intake and risk of prostate cancer: a meta-analysis of observational studies.

    Science.gov (United States)

    Guo, K; Liang, Z; Liu, L; Li, F; Wang, H

    2016-12-01

    The aim of the study was to assess the association between total flavonoids/flavonoid subclasses intake and prostate cancer risk. Several databases were searched to select eligible studies with predefined criteria. Risk ratios (RRs) with 95% confidence intervals (CIs) were used as the effect size. Publication bias and sensitivity analysis were performed. A total of five studies including four prospective cohort studies and one case-control study were included in the meta-analysis. The pooled result demonstrated a significantly increased risk of prostate cancer with higher intake of total flavonoids (RR = 1.12, 95% CI: 1.02-1.23, P = 0.013). However, sensitivity analysis indicated that there lacked a significant association after removing the study of Wang et al. (RR = 1.17, 95% CI: 0.94-1.46). Subgroup analysis stratified by flavonoids subclasses found that higher intake of anthocyanidins and flavan-3-ols were significantly associated with increased prostate cancer risk (RR = 1.12, 95% CI: 1.03-1.21, P = 0.011; RR = 1.21, 95% CI: 1.10-1.32, P flavonoids may not be associated with prostate cancer risk. © 2016 Blackwell Verlag GmbH.

  10. Effects of Dietary Flavonoids on Reverse Cholesterol Transport, HDL Metabolism, and HDL Function.

    Science.gov (United States)

    Millar, Courtney L; Duclos, Quinn; Blesso, Christopher N

    2017-03-01

    Strong experimental evidence confirms that HDL directly alleviates atherosclerosis. HDL particles display diverse atheroprotective functions in reverse cholesterol transport (RCT), antioxidant, anti-inflammatory, and antiapoptotic processes. In certain inflammatory disease states, however, HDL particles may become dysfunctional and proatherogenic. Flavonoids show the potential to improve HDL function through their well-documented effects on cellular antioxidant status and inflammation. The aim of this review is to summarize the basic science and clinical research examining the effects of dietary flavonoids on RCT and HDL function. Based on preclinical studies that used cell culture and rodent models, it appears that many flavonoids (e.g., anthocyanidins, flavonols, and flavone subclasses) influence RCT and HDL function beyond simple HDL cholesterol concentration by regulating cellular cholesterol efflux from macrophages and hepatic paraoxonase 1 expression and activity. In clinical studies, dietary anthocyanin intake is associated with beneficial changes in serum biomarkers related to HDL function in a variety of human populations (e.g., in those who are hyperlipidemic, hypertensive, or diabetic), including increased HDL cholesterol concentration, as well as HDL antioxidant and cholesterol efflux capacities. However, clinical research on HDL functionality is lacking for some flavonoid subclasses (e.g., flavanols, flavones, flavanones, and isoflavones). Although there has been a tremendous effort to develop HDL-targeted drug therapies, more research is warranted on how the intake of foods or specific nutrients affects HDL function. © 2017 American Society for Nutrition.

  11. The effects of heat treatment on the phenolic composition and antioxidant capacity of red wine pomace seasonings.

    Science.gov (United States)

    Del Pino-García, Raquel; González-SanJosé, María L; Rivero-Pérez, María D; García-Lomillo, Javier; Muñiz, Pilar

    2017-04-15

    The impact of thermal processing on the phenolic profile and antioxidant capacity (TAC) of powdered red wine pomace seasonings (RWPSs) obtained from different sources (seedless: Sk-S; whole: W-S; seeds: Sd-S) was assessed. High contents in anthocyanins, flavonol-3-O-glycosides, phenolic acids and flavan-3-ols were found in Sk-S, whereas flavan-3-ols and phenolic acids were the main compounds identified in Sd-S. Reductions in the anthocyanidin and flavonol-3-ol contents mainly determined the effect of heat on the total phenolic contents (Sk-S: -29.4%; W-S: -28.0%; Sd-S: -5.78%), although heating affected positively the phenolic acid and flavonol aglycon contents. Slight TAC decreases were observed in the RWPS-derived extracts (classical Folin-Ciocalteu and ABTS assays). However, higher TAC reductions were detected when the powdered RWPSs were used directly as samples (QUENCHER approach). In conclusion, there is little evidence against submitting RWPSs to thermal processing, as heating affects differently each type of phenolic compound and does not induce very severe TAC decreases in these seasonings. Copyright © 2016 Elsevier Ltd. All rights reserved.

  12. Alternative SNP detection platforms, HRM and biosensors, for varietal identification in Vitis vinifera L. using F3H and LDOX genes.

    Science.gov (United States)

    Gomes, Sónia; Castro, Cláudia; Barrias, Sara; Pereira, Leonor; Jorge, Pedro; Fernandes, José R; Martins-Lopes, Paula

    2018-04-11

    The wine sector requires quick and reliable methods for Vitis vinifera L. varietal identification. The number of V. vinifera varieties is estimated in about 5,000 worldwide. Single Nucleotide Polymorphisms (SNPs) represent the most basic and abundant form of genetic sequence variation, being adequate for varietal discrimination. The aim of this work was to develop DNA-based assays suitable to detect SNP variation in V. vinifera, allowing varietal discrimination. Genotyping by sequencing allowed the detection of eleven SNPs on two genes of the anthocyanin pathway, the flavanone 3-hydroxylase (F3H, EC: 1.14.11.9), and the leucoanthocyanidin dioxygenase (LDOX, EC 1.14.11.19; synonym anthocyanidin synthase, ANS) in twenty V. vinifera varieties. Three High Resolution Melting (HRM) assays were designed based on the sequencing information, discriminating five of the 20 varieties: Alicante Bouschet, Donzelinho Tinto, Merlot, Moscatel Galego and Tinta Roriz. Sanger sequencing of the HRM assay products confirmed the HRM profiles. Three probes, with different lengths and sequences, were used as bio-recognition elements in an optical biosensor platform based on a long period grating (LPG) fiber optic sensor. The label free platform detected a difference of a single SNP using genomic DNA samples. The two different platforms were successfully applied for grapevine varietal identification.

  13. Flavonoids and the CNS

    Directory of Open Access Journals (Sweden)

    Anna K. Jäger

    2011-02-01

    Full Text Available Flavonoids are present in almost all terrestrial plants, where they provide UV-protection and colour. Flavonoids have a fused ring system consisting of an aromatic ring and a benzopyran ring with a phenyl substituent. The flavonoids can be divided into several classes depending on their structure. Flavonoids are present in food and medicinal plants and are thus consumed by humans. They are found in plants as glycosides. Before oral absorption, flavonoids undergo deglycosylation either by lactase phloridzin hydrolase or cytosolic β-glucocidase. The absorbed aglycone is then conjugated by methylation, sulphatation or glucuronidation. Both the aglycones and the conjugates can pass the blood-brain barrier. In the CNS several flavones bind to the benzodiazepine site on the GABAA-receptor resulting in sedation, anxiolytic or anti-convulsive effects. Flavonoids of several classes are inhibitors of monoamine oxidase A or B, thereby working as anti-depressants or to improve the conditions of Parkinson’s patients. Flavanols, flavanones and anthocyanidins have protective effects preventing inflammatory processes leading to nerve injury. Flavonoids seem capable of influencing health and mood.

  14. Genes up-regulated during red coloration in UV-B irradiated lettuce leaves.

    Science.gov (United States)

    Park, Jong-Sug; Choung, Myoung-Gun; Kim, Jung-Bong; Hahn, Bum-Soo; Kim, Jong-Bum; Bae, Shin-Chul; Roh, Kyung-Hee; Kim, Yong-Hwan; Cheon, Choong-Ill; Sung, Mi-Kyung; Cho, Kang-Jin

    2007-04-01

    Molecular analysis of gene expression differences between green and red lettuce leaves was performed using the SSH method. BlastX comparisons of subtractive expressed sequence tags (ESTs) indicated that 7.6% of clones encoded enzymes involved in secondary metabolism. Such clones had a particularly high abundance of flavonoid-metabolism proteins (6.5%). Following SSH, 566 clones were rescreened for differential gene expression using dot-blot hybridization. Of these, 53 were found to overexpressed during red coloration. The up-regulated expression of six genes was confirmed by Northern blot analyses. The expression of chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), and dihydroflavonol 4-reductase (DFR) genes showed a positive correlation with anthocyanin accumulation in UV-B-irradiated lettuce leaves; flavonoid 3',5'-hydroxylase (F3',5'H) and anthocyanidin synthase (ANS) were expressed continuously in both samples. These results indicated that the genes CHS, F3H, and DFR coincided with increases in anthocyanin accumulation during the red coloration of lettuce leaves. This study show a relationship between red coloration and the expression of up-regulated genes in lettuce. The subtractive cDNA library and EST database described in this study represent a valuable resource for further research for secondary metabolism in the vegetable crops.

  15. The catechin flavonoid reduces proliferation and induces apoptosis of murine lymphoma cells LB02 through modulation of antiapoptotic proteins

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    Daniela Laura Papademetrio

    2013-06-01

    Full Text Available Flavonoids are products of secondary metabolism of plants. They are present in herbs and trees and also act as natural chemopreventives and anticancer agents. Ligaria cuneifolia (Ruiz & Pav. Tiegh., Loranthaceae, is a hemiparasite species that belongs to Argentine flora. Phytochemical studies have disclosed the presence of quercetin, catechin-4β-ol and pro-anthocyanidine as polyphenolic compounds in the active extracts. We previously demonstrated that ethyl acetate extract was capable of reducing cell proliferation and inducing apoptotic death of lymphoid tumor cells. The aim of the current study is to determine whether or not catechin, isolated from L. cuneifolia extracts can induce leukemia cell death and to determine its effect on the cytoplasmatic proteins that modulate cell survival. Our results show that catechin can reduce proliferation of murine lymphoma cell line LB02. The effect is mediated by apoptosis at concentrations upper to 100 µg/mL. Cell death is related to the loss of mitochondrial membrane potential (ΔΨm and a down regulation of survivin and Bcl-2 together with the increase of pro-apoptotic protein Bax. In summary, the current study indicates that catechin present in the extract of L. cuneifolia is in part, responsible for the anti-proliferative activity of whole extracts by induction of ΔΨm disruption and modulation of the anti-apoptotic proteins over expressed in tumor cells. These results give new findings into the potential anticancer and chemopreventive activities of L. cuneifolia.

  16. The catechin flavonoid reduces proliferation and induces apoptosis of murine lymphoma cells LB02 through modulation of antiapoptotic proteins

    Directory of Open Access Journals (Sweden)

    Daniela Laura Papademetrio

    2013-03-01

    Full Text Available Flavonoids are products of secondary metabolism of plants. They are present in herbs and trees and also act as natural chemopreventives and anticancer agents. Ligaria cuneifolia (Ruiz & Pav. Tiegh., Loranthaceae, is a hemiparasite species that belongs to Argentine flora. Phytochemical studies have disclosed the presence of quercetin, catechin-4β-ol and pro-anthocyanidine as polyphenolic compounds in the active extracts. We previously demonstrated that ethyl acetate extract was capable of reducing cell proliferation and inducing apoptotic death of lymphoid tumor cells. The aim of the current study is to determine whether or not catechin, isolated from L. cuneifolia extracts can induce leukemia cell death and to determine its effect on the cytoplasmatic proteins that modulate cell survival. Our results show that catechin can reduce proliferation of murine lymphoma cell line LB02. The effect is mediated by apoptosis at concentrations upper to 100 µg/mL. Cell death is related to the loss of mitochondrial membrane potential (ΔΨm and a down regulation of survivin and Bcl-2 together with the increase of pro-apoptotic protein Bax. In summary, the current study indicates that catechin present in the extract of L. cuneifolia is in part, responsible for the anti-proliferative activity of whole extracts by induction of ΔΨm disruption and modulation of the anti-apoptotic proteins over expressed in tumor cells. These results give new findings into the potential anticancer and chemopreventive activities of L. cuneifolia.

  17. Transcriptional analysis of apple fruit proanthocyanidin biosynthesis

    Science.gov (United States)

    Henry-Kirk, Rebecca A.

    2012-01-01

    Proanthocyanidins (PAs) are products of the flavonoid pathway, which also leads to the production of anthocyanins and flavonols. Many flavonoids have antioxidant properties and may have beneficial effects for human health. PAs are found in the seeds and fruits of many plants. In apple fruit (Malus × domestica Borkh.), the flavonoid biosynthetic pathway is most active in the skin, with the flavan-3-ols, catechin, and epicatechin acting as the initiating units for the synthesis of PA polymers. This study examined the genes involved in the production of PAs in three apple cultivars: two heritage apple cultivars, Hetlina and Devonshire Quarrenden, and a commercial cultivar, Royal Gala. HPLC analysis shows that tree-ripe fruit from Hetlina and Devonshire Quarrenden had a higher phenolic content than Royal Gala. Epicatechin and catechin biosynthesis is under the control of the biosynthetic enzymes anthocyanidin reductase (ANR) and leucoanthocyanidin reductase (LAR1), respectively. Counter-intuitively, real-time quantitative PCR analysis showed that the expression levels of Royal Gala LAR1 and ANR were significantly higher than those of both Devonshire Quarrenden and Hetlina. This suggests that a compensatory feedback mechanism may be active, whereby low concentrations of PAs may induce higher expression of gene transcripts. Further investigation is required into the regulation of these key enzymes in apple. Abbreviations:ANOVAanalysis of varianceANRanthocyanidin reductaseDADdiode array detectorDAFBdays after full bloomDFRdihydroflavonol reductaseLARleucoanthocyanidin reductaseLC-MSliquid chromatography/mass spectrometryPAproanthocyanidinqPCRreal-time quantitative PCR PMID:22859681

  18. Characterization and cardioprotective activity of anthocyanins from Nitraria tangutorum Bobr. by-products.

    Science.gov (United States)

    Zhang, Ming; Ma, Jianbin; Bi, Hongtao; Song, Jiayin; Yang, Hongxia; Xia, Zhenghua; Du, Yuzhi; Gao, Tingting; Wei, Lixin

    2017-08-01

    The Nitraria tangutorum Bobr. fruit is an indigenous berry of the shrub belonging to the Zygophyllaceae family which grows at an altitude of over 3000 m in the Tibetan Plateau, and has been used as a native medicinal food for treating weakness of the spleen, stomach syndrome, dyspepsia, neurasthenia, dizziness, etc. for thousands of years. Nowadays, N. tangutorum industrial juice by-products generated from health food production can be a potential low cost source of some unique bioactive ingredients. In a prior study, we established a simultaneous microwave/ultrasonic assisted enzymatic extraction method for extracting antioxidant ingredients from the industrial by-products of N. tangutorum juice. In this study, these ingredients were selectively fractionated by cation-exchange resin chromatography to obtain an anthocyanin fraction namely NJBAE. NJBAE was found to be composed of 16 anthocyanins derived from six anthocyanidins by HPLC-ESI-MS, and has an appreciable cardioprotective effect on doxorubicin-induced injured H9c2 cardiomyocytes. The cardioprotective mechanism research showed that NJBAE could directly scavenge ROS, restrict further generation of ROS, promote the activity of key antioxidase, enhance glutathione redox cycling, then affect the apoptotic signaling changes in a positive way, and finally mediate caspase-dependent cell death pathways. Therefore, NJBAE has great potential to be used for preventing and treating cardiovascular disease in the food, pharmaceutical and other emerging industries.

  19. A New Solid Phase Extraction for the Determination of Anthocyanins in Grapes

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    Marta Ferreiro-González

    2014-12-01

    Full Text Available A method for the concentration and cleaning of red grape extracts prior to the determination of anthocyanins by UPLC-DAD has been developed. This method is of special interest in the determination of phenolic maturity as it allows the analysis of the anthocyanins present in grapes. Several different SPE cartridges were assessed, including both C-18- and vinylbenzene-based cartridges. C-18-based cartridges presented a very low retention for the glucosylated anthocyanidins while vinylbenzene-based cartridges showed excellent retention for these compounds. The optimized method involves the initial conditioning of the cartridge using 10 mL of methanol and 10 mL of water, followed by loading of up to 100 mL of red grape extract. Ten mL of water was used in the washing step and anthocyanins were subsequently eluted using 1.5 mL of acidified methanol at pH 2. This method simplifies the determination of individual anthocyanins as, on the one hand, it cleans the sample of interference and, on the other hand, it increases the concentration to up to 25:1.5. The developed method has been validated with a range of different grapes and it has also been tested as a means of determining the different anthocyanins in grapes with different levels of maturity.

  20. Effect of fermentation and sterilization on anthocyanins in blueberry.

    Science.gov (United States)

    Nie, Qixing; Feng, Lei; Hu, Jielun; Wang, Sunan; Chen, Haihong; Huang, Xiaojun; Nie, Shaoping; Xiong, Tao; Xie, Mingyong

    2017-03-01

    Blueberry products have various health benefits due to their high content of dietary anthocyanins. The aim of this study was to investigate the impact of fermentation and sterilization on total anthocyanin content, composition and some quality attributes of blueberry puree. The blueberry puree used here was fermented for 40 h at 37 °C by Lactobacillus after sterilization. The method of ultra-performance liquid chromatography-mass spectrometry was optimized for the rapid analysis of anthocyanins. Quality attributes including pH, color, total soluble solids and viscosity were measured. A total of 21 anthocyanins and five anthocyanidins were quantified by ultra-performance liquid chromatography. Fermented blueberry had reduced total anthocyanin content (29%) and levels of individual anthocyanins compared with fresh blueberry. Total anthocyanin content was decreased 46% by sterilization, and different degradation behavior of individual anthocyanin was appeared between fermented and sterilized-fermented blueberry puree. Fermentation and sterilization decreased the total soluble solids and pH and changed color parameters, while minimally influencing viscosity. The loss of total anthocyanin content by fermentation was related to the unstable structure of blueberry anthocyanins. Anthocyanins are sensitive to temperature (>80 °C), and degradation of anthocyanins by sterilization in blueberry should be considered in the fermentation procedure. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

  1. Enhanced task-related brain activation and resting perfusion in healthy older adults after chronic blueberry supplementation.

    Science.gov (United States)

    Bowtell, Joanna L; Aboo-Bakkar, Zainie; Conway, Myra E; Adlam, Anna-Lynne R; Fulford, Jonathan

    2017-07-01

    Blueberries are rich in flavonoids, which possess antioxidant and anti-inflammatory properties. High flavonoid intakes attenuate age-related cognitive decline, but data from human intervention studies are sparse. We investigated whether 12 weeks of blueberry concentrate supplementation improved brain perfusion, task-related activation, and cognitive function in healthy older adults. Participants were randomised to consume either 30 mL blueberry concentrate providing 387 mg anthocyanidins (5 female, 7 male; age 67.5 ± 3.0 y; body mass index, 25.9 ± 3.3 kg·m -2 ) or isoenergetic placebo (8 female, 6 male; age 69.0 ± 3.3 y; body mass index, 27.1 ± 4.0 kg·m -2 ). Pre- and postsupplementation, participants undertook a battery of cognitive function tests and a numerical Stroop test within a 1.5T magnetic resonance imaging scanner while functional magnetic resonance images were continuously acquired. Quantitative resting brain perfusion was determined using an arterial spin labelling technique, and blood biomarkers of inflammation and oxidative stress were measured. Significant increases in brain activity were observed in response to blueberry supplementation relative to the placebo group within Brodmann areas 4/6/10/21/40/44/45, precuneus, anterior cingulate, and insula/thalamus (p blueberry versus placebo supplementation (p = 0.05). Supplementation with an anthocyanin-rich blueberry concentrate improved brain perfusion and activation in brain areas associated with cognitive function in healthy older adults.

  2. Effect of the prefermentative addition of five enological tannins on anthocyanins and color in red wines.

    Science.gov (United States)

    Liu, Yan-Xia; Liang, Na-Na; Wang, Jun; Pan, Qiu-Hong; Duan, Chang-Qing

    2013-01-01

    The effects of prefermentation addition of 5 exogenous tannins with different-origin anthocyanins and color characteristics were investigated in "Cabernet Sauvignon wines" at the end of alcoholic fermentation and the end of malolactic fermentation, and after 6 mo and 9 mo of bottle aging, respectively. The results showed that the application of GSKT2 could significantly retard the degradation of most anthocyanins in the process of alcoholic fermentation and the decrease of some pyranoanthocyanins during the subsequent 3 stages, thus causing more yellowness of wine in comparison with the control. Three other condensed tannins, GSKT1, QUET, and GSET, had a positive impact only on several anthocyanin components. Four condensed tannins all contributed to more redness, suggesting that the action mechanism might be to protect wine against oxidation or contribute to form copigmented anthocyanidins, or polymeric pigments. The application of FOLT (hydrolysable tannin) did not produce any influence on wine redness even after 9 mo of bottle aging. This work provides some reasons for the reasonable application of tannin additives. The prefermentative application of condensed tannins overall could protect some pigment components from degradation and enhance wine redness. Tannin additives with different origins have different effectiveness. The tannin additive obtained from grape skins, like GSKT2, could produce significant promotion on both redness and yellowness in wine. The prefermentation addition of hydroxylase tannin like FOLT seems not to have a significant effect on wine color. © 2012 Institute of Food Technologists®

  3. Pharmacokinetics of table and Port red wine anthocyanins: a crossover trial in healthy men.

    Science.gov (United States)

    Fernandes, I; Marques, C; Évora, A; Cruz, L; de Freitas, V; Calhau, C; Faria, A; Mateus, N

    2017-05-24

    This study was designed to evaluate the pharmacokinetics of Port and table red wine anthocyanins in healthy men. Volunteers were recruited to drink 250 mL of a table red wine (221 mg of anthocyanins) and 150 mL of young Port red wine (49 mg of anthocyanins). Venous blood was collected from participants at 0, 15, 30, 60 and 120 min after wine ingestion. Urine samples were collected at baseline and at 120 min. Anthocyanins and anthocyanin metabolites in plasma and urine samples were quantified by HPLC-DAD and tentatively identified by LC-MS. Red wine anthocyanins were detected in their intact forms in both plasma and urine samples, but the glucuronylated metabolites of peonidin and malvidin (PnGlucr and MvGlucr) were the two main derivatives detected after both red wine consumptions. For the first time, and supported by the synthesis of Mv3Glucr, the main pathway followed by Mv3glc after absorption was described and involves anthocyanidin conjugation with glucuronic acid after glucose removal. Despite the lower total content of anthocyanins ingested when volunteers drank Port wine, no differences were observed in the plasma C max of MvGlucr and PnGlucr after table and Port red wine consumption. The relative bioavailability of anthocyanins in Port wine was 96.58 ± 5.74%, compared to the anthocyanins present in red wine. In conclusion, both Port and table red wines are good sources of bioavailable anthocyanins.

  4. FLAVONOID NATURAL SOURCES AND THEIR IMPORTANCE IN THE HUMAN DIET

    Directory of Open Access Journals (Sweden)

    Martina Danihelová

    2011-12-01

    Full Text Available Flavonoids as natural bioactive compounds are present in almost every sort of fruits, vegetables and from them derived products. Flavonols may be found mainly in fruits and vegetables, while flavones are abundant in herbs and spices. Rich natural sources of flavanols are tea, cocoa, grape seeds or apple skin. Flavanones are primarily found in a variety of citrus fruits and anthocyanidins in many coloured berries. Soy is rich in isoflavonoids. Average daily intake of flavonoids is approximately in the range of 150 to 300 mg. It strongly depends on individual, country and culture usages. In west countries main dietary sources of flavonoids consist of tea, wine and fruits, while in east countries there is consumed mainly soy with high isoflavonoid content. Many studies have shown, that intake of fruits and vegetables with high flavonoid content is associated with lowered risk of incidence of some diseases such as cardiovascular or cancer. These findings are attributed to experimentally confirmed biological effects of flavonoids - antioxidant, anti-inflammatory, anti-allergic, anticancer or cardioprotective. The final effect is however depending on their bioavailability, which is in the case of flavonoids not high, because in the nature dominating flavonoid glycosides can poorly penetrate through lipophilic cell membranes. Final effective molecules are flavonoid metabolites, that more or less retain their biological activities. doi: 10.5219/160

  5. IDENTIFIKASI ANTOSIANIN BUAH DUWET (Syzygium cumini MENGGUNAKAN KROMATOGRAFI CAIR KINERJA TINGGI - DIODE ARRAY DETECTION [Identification of Anthocyanins in Jambolan Fruit (Syzygium cumini by High Performance Liquid Chromatography - Diode Array Detection

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    Puspita Sari1*

    2009-12-01

    Full Text Available The aim of this study was to determine the content of total monomeric anthocyanins and to identify the anthocyanin composition of jambolan fruit (Syzygium cumini growing in Indonesia. Anthocyanins were extracted with methanol containing 0.1% HCl, removed from non-polar impurities by partition with chloroform and purified in a C18 solid phase cartridge. Anthocyanins were identified by high-performance liquid chromatography with diode array detection (HPLC-DAD, UV-visible spectral analysis, and physico-chemical reactions. Using pH-differential method, it was known that the content of total monomeric anthocyanin in the ripe fruit was 161 mg/100 g fresh fruit (731 mg/100 g skin on wet basis or 3430 mg/100 g skin on dry basis, based on cyanidin-3-glucoside. Furthermore, five anthocyanins without acylating groups were identified as 3,5-diglucoside derivatives of delphinidin (41.29%, petunidin (27.79%, malvidin (25.60%, cyanidin (4.19%, and peonidin (1.13%. These results demonstrate that the skin of jambolan fruit especially the ripe one is rich in anthocyanin, with wide range in anthocyanidin backbone (five aglycons.

  6. Antioxidant Activity in Extracts of 27 Indigenous Taiwanese Vegetables

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    Pi-Yu Chao

    2014-05-01

    Full Text Available The objectives of this study were to identify the antioxidants and antioxidant axtivity in 27 of Taiwan’s indigenous vegetables. Lycium chinense (Lc, Lactuca indica (Li, and Perilla ocymoides (Po contained abundant quercetin (Que, while Artemisia lactiflora (Al and Gynura bicolor (Gb were rich in morin and kaempferol, respectively. Additionally, Nymphoides cristata (Nc and Sechium edule (Se-yellow had significantly higher levels of myricetin (Myr than other tested samples. Cyanidin (Cyan and malvidin (Mal were abundant in Gb, Abelmoschus esculentus Moench (Abe, Po, Anisogonium esculentum (Retz. Presl (Ane, Ipomoea batatas (Ib-purple, and Hemerocallis fulva (Hf-bright orange. Relatively high levels of Trolox equivalent antioxidant capacity (TEAC, oxygen radical absorption capacity (ORAC, and 1,1-diphenyl-2-picryl-hydrazyl (DPPH radical scavenger were generated from extracts of Toona sinensis (Ts and Po. Significant and positive correlations between antioxidant activity and polyphenols, anthocyanidins, Que, Myr, and morin were observed, indicating that these phytochemicals were some of the main components responsible for the antioxidant activity of tested plants. The much higher antioxidant activity of Po, Ts, and Ib (purple leaf may be related to their higher Cyan, Que, and polyphenol content.

  7. Extracts, Anthocyanins and Procyanidins from Aronia melanocarpa as Radical Scavengers and Enzyme Inhibitors

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    Hilde Barsett

    2013-03-01

    Full Text Available Extracts, subfractions, isolated anthocyanins and isolated procyanidins B2, B5 and C1 from the berries and bark of Aronia melanocarpa were investigated for their antioxidant and enzyme inhibitory activities. Four different bioassays were used, namely scavenging of the diphenylpicrylhydrazyl (DPPH radical, inhibition of 15-lipoxygenase (15-LO, inhibition of xanthine oxidase (XO and inhibition of α-glucosidase. Among the anthocyanins, cyanidin 3-arabinoside possessed the strongest and cyanidin 3-xyloside the weakest radical scavenging and enzyme inhibitory activity. These effects seem to be influenced by the sugar units linked to the anthocyanidin. Subfractions enriched in procyanidins were found to be potent α-glucosidase inhibitors; they possessed high radical scavenging properties, strong inhibitory activity towards 15-LO and moderate inhibitory activity towards XO. Trimeric procyanidin C1 showed higher activity in the biological assays compared to the dimeric procyanidins B2 and B5. This study suggests that different polyphenolic compounds of A. melanocarpa can have beneficial effects in reducing blood glucose levels due to inhibition of α-glucosidase and may have a potential to alleviate oxidative stress.

  8. Flavonoids Promote Haustoria Formation in the Root Parasite Triphysaria versicolor1

    Science.gov (United States)

    Albrecht, Huguette; Yoder, John I.; Phillips, Donald A.

    1999-01-01

    Parasitic plants in the Scrophulariaceae develop infective root structures called haustoria in response to chemical signals released from host-plant roots. This study used a simple in vitro assay to characterize natural and synthetic molecules that induce haustoria in the facultative parasite Triphysaria versicolor. Several phenolic acids, flavonoids, and the quinone 2,6-dimethoxy-p-benzoquinone induced haustoria in T. versicolor root tips within hours after treatment. The concentration at which different molecules were active varied widely, the most active being 2,6-dimethoxy-p-benzoquinone and the anthocyanidin peonidin. Maize (Zea mays) seeds are rich sources of molecules that induce T. versicolor haustoria in vitro, and chromatographic analyses indicated that the active molecules present in maize-seed rinses include anthocyanins, other flavonoids, and simple phenolics. The presence of different classes of inducing molecules in seed rinses was substantiated by the observation that maize kernels deficient in chalcone synthase, a key enzyme in flavonoid biosynthesis, released haustoria-inducing molecules, although at reduced levels compared with wild-type kernels. We discuss these results in light of existing models for host perception in the related parasitic plant Striga. PMID:9952454

  9. Chemistry of Secondary Polyphenols Produced during Processing of Tea and Selected Foods

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    Takashi Tanaka

    2009-12-01

    Full Text Available This review will discuss recent progress in the chemistry of secondary polyphenols produced during food processing. The production mechanism of the secondary polyphenols in black tea, whisky, cinnamon, and persimmon fruits will be introduced. In the process of black tea production, tea leaf catechins are enzymatically oxidized to yield a complex mixture of oxidation products, including theaflavins and thearubigins. Despite the importance of the beverage, most of the chemical constituents have not yet been confirmed due to the complexity of the mixture. However, the reaction mechanisms at the initial stages of catechin oxidation are explained by simple quinone–phenol coupling reactions. In vitro model experiments indicated the presence of interesting regio- and stereoselective reactions. Recent results on the reaction mechanisms will be introduced. During the aging of whisky in oak wood barrels, ellagitannins originating from oak wood are oxidized and react with ethanol to give characteristic secondary ellagitannins. The major part of the cinnamon procyanidins is polymerized by copolymerization with cinnamaldehyde. In addition, anthocyanidin structural units are generated in the polymer molecules by oxidation which accounts for the reddish coloration of the cinnamon extract. This reaction is related to the insolubilization of proanthocyanidins in persimmon fruits by condensation with acetaldehyde. In addition to oxidation, the reaction of polyphenols with aldehydes may be important in food processing.

  10. Anthocyanin characteristics of wines in Vitis germplasms cultivated in southern China

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    Guo CHENG

    2017-10-01

    Full Text Available Abstract The anthocyanin profiles and CIELAB color values of nine wines in Vitis germplasms from southern China were compared. The results showed that the anthocyanin composition of wines from one hybrid between V. vinifera and V. labrusca (‘Moldova’, two V. labrusca varieties (‘Conquistador’ and ‘Saint-Croix’, one V. quinquangularis variety (‘Yeniang No.2’, one hybrid between V. quinquangularis and V. vinifera (‘NW196’, one V. davidii variety (‘Xiangniang No.1’ and one V. rotundifolia variety (‘Noble’ were dominated by anthocyanidin 3,5-O-diglucosides. All these were quite different from V. vinifera wines (‘Cabernet Sauvignon’ and ‘Marselan’, which were characterized by the monoglucoside and pyranoanthocyanins. 3',4',5'-substituted anthocyanins were dominant in the wines of all varieties, except ‘Noble’ wine. ‘Yeniang No.2’ (V. quinquangularis had the highest acid, total anthocyanin concentration, and showed a more intense pigmentation with a higher proportion and concentration of coumaroylated anthocyanins. In the colorimetric analysis, ‘Yeniang No.2’ (V. quinquangularis wine showed the most saturated red colors, followed by ‘NW196’ (V. quinquangularis. The detected chromatic characteristics of these wines were basically in accordance with their sensory evaluation.

  11. Chlorogenic acid, anthocyanin and flavan-3-ol biosynthesis in flesh and skin of Andean potato tubers (Solanum tuberosum subsp. andigena).

    Science.gov (United States)

    Valiñas, Matías Ariel; Lanteri, María Luciana; Ten Have, Arjen; Andreu, Adriana Balbina

    2017-08-15

    Natural variation of Andean potato was used to study the biosynthesis of phenolic compounds. Levels of phenolic compounds and corresponding structural gene transcripts were examined in flesh and skin of tubers. Phenolic acids, mainly chlorogenic acid (CGA), represent the major compounds, followed by anthocyanins and flavan-3-ols. High-anthocyanin varieties have high levels of CGA. Both metabolite and transcript levels were higher in skin than in flesh and showed a good correspondence. Two hydroxycinnamoyl-CoA transferases (HCT/HQT) have been involved in CGA production, of which HCT reflects CGA levels. Catechin was found in pigmented tissues whereas epicatechin was restricted to tuber skin. Transcripts of leucoanthocyanidin reductase (LCR), which generates catechin, could not be detected. Anthocyanidin reductase (ANR) transcripts, the enzyme responsible for epicatechin production, showed similar levels among samples. These data suggest that the biosynthesis of flavan-3-ols in potato tuber would require ANR but not LCR and that an epimerization process is involved. Copyright © 2017 Elsevier Ltd. All rights reserved.

  12. Investigation of Antioxidant Activity of Pomegranate Juices by Means of Electron Paramagnetic Resonance and UV-Vis Spectroscopy.

    Science.gov (United States)

    Kozik, Violetta; Jarzembek, Krystyna; Jędrzejowska, Agnieszka; Bąk, Andrzej; Polak, Justyna; Bartoszek, Mariola; Pytlakowska, Katarzyna

    2015-01-01

    Pomegranate fruit (Punica granatum L.) is a source of numerous phenolic compounds, and it contains flavonoids such as anthocyanins, anthocyanidins, cyanidins, catechins and other complexes of flavonoids, ellagitannins, and hydrolyzed tannins. Pomegranate juice shows antioxidant, antiproliferative, and anti-atherosclerotic properties. The antioxidant capacity (TEAC) of the pomegranate juices was measured using electron paramagnetic resonance (EPR) spectroscopy and 1,1-diphenyl-2-picrylhydrazyl (DPPH•) as a source of free radicals, and the total phenolic (TP) content was measured using UV-Vis spectroscopy. All the examined pomegranate juices exhibited relatively high antioxidant properties. The TEAC values determined by means of EPR spectroscopy using Trolox (TE) as a free radical scavenger were in the range of 463.12 to 1911.91 μmol TE/100 mL juice. The TP content measured by the Folin-Ciocalteu method, using gallic acid (GA) as a free radical scavenger, widely varied in the investigated pomegranate juice samples and ranged from 1673.62 to 5263.87 mg GA/1 L juice. The strongest antioxidant properties were observed with the fresh pomegranate juices obtained from the fruits originating from Israel, Lebanon, and Azerbaijan. Correlation analysis of numerical data obtained by means of EPR spectroscopy (TEAC) and UV-Vis spectroscopy (TP) gave correlation coefficient (r)=0.90 and determination coefficient (r2)=0.81 (P<0.05).

  13. Preventive and Prophylactic Mechanisms of Action of Pomegranate Bioactive Constituents

    Science.gov (United States)

    Viladomiu, Monica; Hontecillas, Raquel; Lu, Pinyi; Bassaganya-Riera, Josep

    2013-01-01

    Pomegranate fruit presents strong anti-inflammatory, antioxidant, antiobesity, and antitumoral properties, thus leading to an increased popularity as a functional food and nutraceutical source since ancient times. It can be divided into three parts: seeds, peel, and juice, all of which seem to have medicinal benefits. Several studies investigate its bioactive components as a means to associate them with a specific beneficial effect and develop future products and therapeutic applications. Many beneficial effects are related to the presence of ellagic acid, ellagitannins (including punicalagins), punicic acid and other fatty acids, flavonoids, anthocyanidins, anthocyanins, estrogenic flavonols, and flavones, which seem to be its most therapeutically beneficial components. However, the synergistic action of the pomegranate constituents appears to be superior when compared to individual constituents. Promising results have been obtained for the treatment of certain diseases including obesity, insulin resistance, intestinal inflammation, and cancer. Although moderate consumption of pomegranate does not result in adverse effects, future studies are needed to assess safety and potential interactions with drugs that may alter the bioavailability of bioactive constituents of pomegranate as well as drugs. The aim of this review is to summarize the health effects and mechanisms of action of pomegranate extracts in chronic inflammatory diseases. PMID:23737845

  14. Molecular characterization of genes encoding leucoanthocyanidin reductase involved in proanthocyanidin biosynthesis in apple

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    Yuepeng eHan

    2015-04-01

    Full Text Available Proanthocyanidins (PAs are the major component of phenolics in apple, but mechanisms involved in PA biosynthesis remain unclear. Here, the relationship between the PA biosynthesis and the expression of genes encoding leucoanthocyanidin reductase (LAR and anthocyanidin reductase (ANR was investigated in fruit skin of one apple cultivar and three crabapples. Transcript levels of LAR1 and ANR2 genes were significantly correlated with the contents of catechin and epicatechin, respectively, which suggests their active roles in PA synthesis. Surprisingly, transcript levels for both LAR1 and LAR2 genes were almost undetectable in two crabapples that accumulated both flavan-3-ols and PAs. This contradicts the previous finding that LAR1 gene is a strong candidate regulating the accumulation of metabolites such as epicatechin and PAs in apple. Ectopic expression of apple MdLAR1 gene in tobacco suppresses expression of the late genes in anthocyanin biosynthetic pathway, resulting in loss of anthocyanin in flowers. Interestingly, a decrease in PA biosynthesis was also observed in flowers of transgenic tobacco plants overexpressing the MdLAR1 gene, which could be attributed to decreased expression of both the NtANR1 and NtANR2 genes. Our study not only confirms the in vivo function of apple LAR1 gene, but it is also helpful for understanding the mechanism of PA biosynthesis.

  15. Flavan-3-ols Are an Effective Chemical Defense against Rust Infection1[OPEN

    Science.gov (United States)

    Unsicker, Sybille B.; Fellenberg, Christin; Schmidt, Axel

    2017-01-01

    Phenolic secondary metabolites are often thought to protect plants against attack by microbes, but their role in defense against pathogen infection in woody plants has not been investigated comprehensively. We studied the biosynthesis, occurrence, and antifungal activity of flavan-3-ols in black poplar (Populus nigra), which include both monomers, such as catechin, and oligomers, known as proanthocyanidins (PAs). We identified and biochemically characterized three leucoanthocyanidin reductases and two anthocyanidin reductases from P. nigra involved in catalyzing the last steps of flavan-3-ol biosynthesis, leading to the formation of catechin [2,3-trans-(+)-flavan-3-ol] and epicatechin [2,3-cis-(−)-flavan-3-ol], respectively. Poplar trees that were inoculated with the biotrophic rust fungus (Melampsora larici-populina) accumulated higher amounts of catechin and PAs than uninfected trees. The de novo-synthesized catechin and PAs in the rust-infected poplar leaves accumulated significantly at the site of fungal infection in the lower epidermis. In planta concentrations of these compounds strongly inhibited rust spore germination and reduced hyphal growth. Poplar genotypes with constitutively higher levels of catechin and PAs as well as hybrid aspen (Populus tremula × Populus alba) overexpressing the MYB134 transcription factor were more resistant to rust infection. Silencing PnMYB134, on the other hand, decreased flavan-3-ol biosynthesis and increased susceptibility to rust infection. Taken together, our data indicate that catechin and PAs are effective antifungal defenses in poplar against foliar rust infection. PMID:29070515

  16. Syzygium Cordatum Hochst. ex Krauss: An Overview of Its Ethnobotany, Phytochemistry and Pharmacological Properties

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    Alfred Maroyi

    2018-05-01

    Full Text Available Syzygium cordatum is a valuable medicinal plant in the materia medica of east and southern Africa. The aim of this study was to review the botany, medicinal uses, phytochemistry and ethnopharmacological properties of S. cordatum. Relevant literature search was carried out using internet sources such as ACS, Web of Science, Wiley, SpringerLink, Scopus, Mendeley, Google Scholar, Pubmed, SciFinder, BioMed Central, Science Direct and Elsevier. Other literature sources were conference papers, book chapters, books, theses and websites. The leaves, roots, bark and fruits of S. cordatum are used as ethnomedicines against 24 human diseases such as gastro-intestinal disorders, burns, sores, wounds, colds, cough, respiratory complaints, sexually transmitted infections (STIs, tuberculosis, fever and malaria. Several phytochemical compounds including alkaloids, anthocyanidin, essential oils, flavonoids, leucoanthocyanidin, phenols, phytosterols, saponins, simple sugars, terpenoids and triterpenoid have been identified from S. cordatum. Pharmacological evaluations revealed that S. cordatum is characterized by several biological activities including antibacterial, antifungal, antidiarrheal, anti-sexually transmitted infections, antidiabetic, anticholinesterase, anti-inflammatory, antileishmanial, antioxidant, antiplasmodial and anti-proteus. These pharmacological findings lend credence to the traditional ethnomedicinal uses and ethnopharmacological importance of S. cordatum. Future research on the species should identify the biological compounds, their mode of action and physiological pathways and clinical relevance.

  17. Analysis of Arabidopsis mutants deficient in flavonoid biosynthesis

    International Nuclear Information System (INIS)

    Shirley, B.W.; Kubasek, W.L.; Storz, G.; Bruggemann, E.; Koornneef, M.; Ausubel, F.M.; Goodman, H.M.

    1995-01-01

    Eleven loci that play a role in the synthesis of flavonoids in Arabidopsis are described. Mutations at these loci, collectively named transparent testa (tt), disrupt the synthesis of brown pigments in the seed coat (testa). Several of these loci (tt3, tt4, tt5 and ttg) are also required for the accumulation of purple anthocyanins in leaves and stems and one locus (ttg) plays additional roles in trichome and root hair development. Specific functions were previously assigned to tt1-7 and ttg. Here, the results of additional genetic, biochemical and molecular analyses of these mutants are described. Genetic map positions were determined for tt8, tt9 and tt10. Thin-layer chromatography identified tissue- and locus-specific differences in the flavonols and anthocyanidins synthesized by mutant and wild-type plants. It was found that UV light reveals distinct differences in the floral tissues of tt3, tt4, tt5, tt6 and ttg, even though these tissues are indistinguishable under visible light. Evidence was also uncovered that tt8 and ttg specifically affect dihydroflavonol reductase gene expression. A summary of these and previously published results are incorporated into an overview of the genetics of flavonoid biosynthesis in Arabidopsis

  18. OBTENÇÃO E UTILIZAÇÃO DA ENZIMA POLIFENOLOXIDASE EXTRAÍDA DE POLPA DE PINHA (Annona squamosa L. MADURA NO MELHORAMENTO DO SABOR DO CACAU (Theobroma cacao L. OBTAINING AND USE OF POLYPHENOLOXIDASE ENZYME EXTRACTED FROM RIPE CUSTARD APPLE (Annona squamosa L. PULP ON THE COCOA (Theobroma cacao L. NIBS IN TASTE IMPROVEMENT

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    ELIZA DOROTEA POZZOBON DE ALBUQUERQUE LIMA

    2001-12-01

    material obtained was called partially purified enzyme, being the analyses of activity carried out with catechol as substract, showing biochemical characteristics of 5.0 to 6.5 stability pH and 10 to 30°C stability temperature the nibs were autoclaved (121°C for 15 minutes and non-autoclaved from the same origin, raw nuts insuficiently fermented and dried were soaked in a solution of the enzyme containing 200 units/min/mL, for 30, 60, 90, 210 and 360 minutes, at 23°C and pH 6.0 . The nibs were homogeneized with the enzyme solution each 15 minutes, dried, ground and became unfatted. After enzymatic treatment over 210 minutes carried out on the non-autoclaved unfatted cocoa nibs, it was possible to observe diminishing of 15% in the total phenol, 15% tannin content, 10% of flavan-3-ois and 18% of anthocyanidins concentrations. The nibs of autoclaved unfatted cacao showed diminishing of 25% in the total phenol, 26% of tannins 23% of flavan-3-ois, and 51% of anthocyanidins concentrations.

  19. Overexpression of CsANR increased flavan-3-ols and decreased anthocyanins in transgenic tobacco.

    Science.gov (United States)

    Kumar, Vinay; Yadav, Sudesh Kumar

    2013-06-01

    Anthocyanins and flavan-3-ols are distributed widely in plants and synthesized by a common biosynthetic pathway. Anthocyanin reductase (ANR) represents branching-point enzyme of this pathway converting anthocyanidins to flavan-3-ols. Since tea contains highest amount of flavonoids, a cDNA encoding anthocyanin reductase from tea (CsANR) was overexpressed in transgenic tobacco to check the influence on anthocyanin and flavan-3-ols. The transgenic tobacco was confirmed by genomic PCR and expression of transgene was analyzed through semiquantitative PCR. Interestingly flowers of transgenic tobacco were light pink/white in color instead of dark pink in wild tobacco, documenting the decrease in anthocyanins content. Upon measurement, flower anthocyanin content was found to be lesser. While flavan-3-ols (epicatechin and epigallocatechin) contents were increased in leaf tissue of transgenic lines. The expressions of other endogenous flavonoid biosynthetic pathway genes in different floral parts (sepal, petal, stamen, and carpel) of CsANR overexpressing tobacco as well as wild tobacco were analyzed. The transcript levels of PAL and CHI genes were downregulated, while transcript levels of F3H, FLS, CHS, ANR1, and ANR2 genes were upregulated in all floral parts of CsANR transgenic plants compared to wild tobacco. The expressions of DFR and ANS genes were also spatially modulated in different floral parts due to overexpression of CsANR. Thus, CsANR overexpression increased flavan-3-ols and decreased anthocyanin content by modulating the expressions of various flavonoid biosynthetic pathway genes in flower of tobacco. These changes might be responsible for the observed pollen tube in the pollens of CsANR overexpressing transgenic tobacco when they were still in the anther before pollination.

  20. Coordinated regulation of anthocyanin biosynthesis in Chinese bayberry (Myrica rubra) fruit by a R2R3 MYB transcription factor.

    Science.gov (United States)

    Niu, Shan-Shan; Xu, Chang-Jie; Zhang, Wang-Shu; Zhang, Bo; Li, Xian; Lin-Wang, Kui; Ferguson, Ian B; Allan, Andrew C; Chen, Kun-Song

    2010-03-01

    Chinese bayberry (Myrica rubra) is a fruit crop with cultivars producing fruit ranging from white (Shuijing, SJ) to red (Dongkui, DK) and dark red-purple (Biqi, BQ), as a result of different levels of anthocyanin accumulation. Genes encoding the anthocyanin biosynthesis enzymes chalcone synthase, chalcone isomerase, flavanone 3-hydroxylase (F3H), flavonoid 3'-hydroxylase (F3'H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS) and UDPglucose: flavonoid 3-O-glucosyltransferase (UFGT), as well as MrMYB1, a R2R3 MYB transcription factor homologous to known activators of anthocyanin biosynthesis, were isolated from ripe fruit of BQ. Differences in mRNA abundance of MrF3H, MrF3'H, MrDFR1, MrANS and MrUFGT were highly correlated with differential accumulation of anthocyanins between cultivars, suggesting coordinated regulation by transcription factors. The transcript level of MrMYB1 was strongly associated with the anthocyanin content in ripe fruit of the three cultivars, as well as different anthocyanin containing tissues of BQ fruit. Fruit bagging strongly inhibited anthocyanin accumulation in fruit as well as the expression of all anthocyanin biosynthetic genes and MrMYB1. Overexpression of MrMYB1 stimulated both anthocyanin accumulation and activated an Arabidopsis-DFR promoter in tobacco (Nicotiana tabacum). MrMYB1d, an allele with a 1 bp deletion at nucleotide 30 of coding sequence, was observed in SJ and DK fruit, suggesting that a nonsense mutation of the MYB1 protein may be responsible for no or low expression of MYB1 in the white and red fruit. These results show that coordinated expression of multiple biosynthetic genes is involved in anthocyanin accumulation in Chinese bayberry fruit, and this is regulated by MrMYB1.

  1. Cloning and characterization of a potato StAN11 gene involved in anthocyanin biosynthesis regulation.

    Science.gov (United States)

    Li, Wang; Wang, Bing; Wang, Man; Chen, Min; Yin, Jing-Ming; Kaleri, Ghullam Murtaza; Zhang, Rui-Jie; Zuo, Tie-Niu; You, Xiong; Yang, Qing

    2014-04-01

    Anthocyanins are a class of products of plant secondary metabolism and are responsible for tubers color in potato. The biosynthesis of anthocyanins is a complex biological process, in which multiple genes are involved including structural genes and regulatory genes. In this study, StAN11, a WD40-repeat gene, was cloned from potato cultivar Chieftain (Solanum tuberosum L.). StAN11 (HQ599506) contained no intron and its open reading frame (ORF) was 1,029 bp long, encoding a putative protein of 342 amino acids. In order to verify its role in anthocyanin biosynthesis, StAN11 was inserted behind the CaMV-35S promoter of pCMBIA1304 and the recombination vector was introduced into the potato cultivar Désirée plants by Agrobacterium-mediated transformation. The color of transgenic tuber skin was significantly deepened, compared to the wild-type control, which was highly consistent with the accumulation of anthocyanin and expression of StAN11 in transgenic lines tuber skin. Further analysis on the expression of Flavonone-3-hydroxylase (F3H), Dihydroflavonol reductase (DFR), Anthocyanidin synthase (ANS), and Flavonoid 3-O-glucosyl transferase (3GT) in transgenic plants revealed that only DFR was upregulated. This result suggested that StAN11 regulated anthocyanin biosynthesis in potato by controlling DFR expression and accumulation of anthocyanin could be increased through overexpression of StAN11 in the tubers with the genetic background of anthocyanin biosynthesis. © 2013 Institute of Botany, Chinese Academy of Sciences.

  2. The sweet potato IbMYB1 gene as a potential visible marker for sweet potato intragenic vector system.

    Science.gov (United States)

    Kim, Cha Young; Ahn, Young Ock; Kim, Sun Ha; Kim, Yun-Hee; Lee, Haeng-Soon; Catanach, Andrew S; Jacobs, Jeanne M E; Conner, Anthony J; Kwak, Sang-Soo

    2010-07-01

    MYB transcription factors play important roles in transcriptional regulation of many secondary metabolites including anthocyanins. We cloned the R2R3-MYB type IbMYB1 complementary DNAs from the purple-fleshed sweet potato (Ipomoea batatas L. cv Sinzami) and investigated the expression patterns of IbMYB1 gene with IbMYB1a and IbMYB1b splice variants in leaf and root tissues of various sweet potato cultivars by reverse transcription-polymerase chain reaction. The transcripts of IbMYB1 were predominantly expressed in the purple-fleshed storage roots and they were also detectable in the leaf tissues accumulating anthocyanin pigments. In addition, transcript levels of IbMYB1 gene were up-regulated by treatment with methyl jasmonate or salicylic acid in leaf and root tissues of cv. White Star. To set up the intragenic vector system in sweet potato, we first evaluated the utilization of the IbMYB1 gene as a visible selectable marker. The IbMYB1a was transiently expressed in tobacco leaves under the control of a constitutive cauliflower mosaic virus 35S promoter, a root-specific and sucrose-inducible sporamin promoter, and an oxidative stress-inducible sweet potato anionic peroxidase2 promoter. We also showed that overexpression of IbMYB1a induced massive anthocyanin pigmentation in tobacco leaves and up-regulated the transcript levels of the structural genes in anthocyanin biosynthetic pathway. Furthermore, high-performance liquid chromatography analysis revealed that the expression of IbMYB1a led to production of cyanidin as a major core molecule of anthocyanidins in tobacco leaves. These results suggest that the IbMYB1 gene can be applicable to a visible marker for sweet potato transformation with intragenic vectors, as well as the production of anthocyanin as important nutritive value in other plant species.

  3. Expression of the sweetpotato R2R3-type IbMYB1a gene induces anthocyanin accumulation in Arabidopsis.

    Science.gov (United States)

    Chu, Hyosub; Jeong, Jae Cheol; Kim, Wook-Jin; Chung, Dong Min; Jeon, Hyo Kon; Ahn, Young Ock; Kim, Sun Ha; Lee, Haeng-Soon; Kwak, Sang-Soo; Kim, Cha Young

    2013-06-01

    R2R3-type MYB transcription factors (TFs) play important roles in transcriptional regulation of anthocyanins. The R2R3-type IbMYB1 is known to be a key regulator of anthocyanin biosynthesis in the storage roots of sweetpotato. We previously showed that transient expression of IbMYB1a led to anthocyanin pigmentation in tobacco leaves. In this article, we generated transgenic Arabidopsis plants expressing the IbMYB1a gene under the control of CaMV 35S promoter, and the sweetpotato SPO and SWPA2 promoters. Overexpression of IbMYBa in transgenic Arabidopsis produced strong anthocyanin pigmentation in seedlings and generated a deep purple color in leaves, stems and seeds. Reverse transcription-polymerase chain reaction analysis showed that IbMYB1a expression induced upregulation of several structural genes in the anthocyanin biosynthetic pathway, including 4CL, CHI, F3'H, DFR, AGT, AAT and GST. Furthermore, overexpression of IbMYB1a led to enhanced expression of the AtTT8 (bHLH) and PAP1/AtMYB75 genes. high-performance liquid chromatography analysis revealed that IbMYB1a expression led to the production of cyanidin as a major core molecule of anthocyanidins in Arabidopsis, as occurs in the purple leaves of sweetpotato (cv. Sinzami). This result shows that the IbMYB1a TF is sufficient to induce anthocyanin accumulation in seedlings, leaves, stems and seeds of Arabidopsis plants. Copyright © Physiologia Plantarum 2012.

  4. In Silico study for diversing the molecular pathway of pigment formation: An alternative to manual coloring in cotton fibers.

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    Ammara eAhad

    2015-09-01

    Full Text Available Diversity of colors in flowers and fruits is largely due to anthocyanin pigments. The flavonoid/anthocyanin pathway has been most extensively studied. Dihydroflavonol 4-reductase (DFR is a vibrant enzyme of the flavonoid pathway which displays major impact on the formation of anthocyanins, flavan 3-ols and flavonols. The substrate specificity of the DFR was found to play a crucial role in determination of type of anthocyanidins. Altering the flavonoid/ anthocyanin pathway through genetic engineering to develop color of our own choice is an exciting subject of future research. In the present study, comparison among four DFR genes (Gossypium hirsutum, Iris × hollandica, Ang. DFRI and DFRII, sequence alignment for homology as well as protein modeling and docking is demonstrated. Estimation of catalytic sites, prediction of substrate preference and protein docking were the key features of this article. For specific substrate uptake, a proline rich region and positions 12 plus 26 along with other positions emphasizing the 26-amino acid residue region (132-157 was tested. Results showed that proline rich region position 12, 26 and 132-157 plays an important role in selective attachment of DFRs with respective substrates. Further, ‘Expasy ProtParam tool’ results showed that Iris × hollandica DFR amino acids (Asn 9: Asp 23 favorable for reducing DHQ and DHM thus accumulating delphinidin, while Gossypium hirsutum DFR has (Asn 13: Asp 21 hypothesized to consume DHK. Protein docking data showed that amino acid residues in above mentioned positions were just involved in attachment of DFR with substrate and had no role in specific substrate uptake.Advanced bioinformatics analysis has revealed that all above mentioned positions have role in substrate attachment. For substrate specificity, other residues region is involved. It will help in color manipulations in different plant species.

  5. Gene Expression and Metabolite Profiling of Developing Highbush Blueberry Fruit Indicates Transcriptional Regulation of Flavonoid Metabolism and Activation of Abscisic Acid Metabolism1[W][OA

    Science.gov (United States)

    Zifkin, Michael; Jin, Alena; Ozga, Jocelyn A.; Zaharia, L. Irina; Schernthaner, Johann P.; Gesell, Andreas; Abrams, Suzanne R.; Kennedy, James A.; Constabel, C. Peter

    2012-01-01

    Highbush blueberry (Vaccinium corymbosum) fruits contain substantial quantities of flavonoids, which are implicated in a wide range of health benefits. Although the flavonoid constituents of ripe blueberries are known, the molecular genetics underlying their biosynthesis, localization, and changes that occur during development have not been investigated. Two expressed sequence tag libraries from ripening blueberry fruit were constructed as a resource for gene identification and quantitative real-time reverse transcription-polymerase chain reaction primer design. Gene expression profiling by quantitative real-time reverse transcription-polymerase chain reaction showed that flavonoid biosynthetic transcript abundance followed a tightly regulated biphasic pattern, and transcript profiles were consistent with the abundance of the three major classes of flavonoids. Proanthocyanidins (PAs) and corresponding biosynthetic transcripts encoding anthocyanidin reductase and leucoanthocyanidin reductase were most concentrated in young fruit and localized predominantly to the inner fruit tissue containing the seeds and placentae. Mean PA polymer length was seven to 8.5 subunits, linked predominantly via B-type linkages, and was relatively constant throughout development. Flavonol accumulation and localization patterns were similar to those of the PAs, and the B-ring hydroxylation pattern of both was correlated with flavonoid-3′-hydroxylase transcript abundance. By contrast, anthocyanins accumulated late in maturation, which coincided with a peak in flavonoid-3-O-glycosyltransferase and flavonoid-3′5′-hydroxylase transcripts. Transcripts of VcMYBPA1, which likely encodes an R2R3-MYB transcriptional regulator of PA synthesis, were prominent in both phases of development. Furthermore, the initiation of ripening was accompanied by a substantial rise in abscisic acid, a growth regulator that may be an important component of the ripening process and contribute to the regulation

  6. Protective activities of Vaccinium antioxidants with potential relevance to mitochondrial dysfunction and neurotoxicity.

    Science.gov (United States)

    Yao, Yu; Vieira, Amandio

    2007-01-01

    Both the neurotransmitter dopamine (DA) and a neurotoxic metabolite, 6-hydroxy DA, can be oxidized to generate hydrogen peroxide and other reactive species (ROS). ROS promote oxidative stress and have been implicated in dopaminergic neurodegeneration, e.g., Parkinson's disease (PD). There is also evidence for a relation between catecholamine-mediated oxidative damage in dopaminergic neurons and the effects of these neurotransmitters on the redox state of cytochrome c (Cytc). In neurons and other cells, oxidative stress may be enhanced by abnormal release of Cytc and other mitochondrial proteins into the cytoplasm. Cytc release can result in apoptosis; but sub-apoptogenic-threshold release can also occur, and may be highly damaging in the presence of DA metabolites. Loss of mitochondrial membrane integrity, a pathological situation of relevance to several aging-related neurodegenerative disorders including PD, contributes to release of Cytc; and the level of such release is known to be indicative of the extent of mitochondrial dysfunction. In this context, we have used a Cytc-enhanced 6-hydroxy DA oxidation reaction to gauge dietary antioxidant activities. Anthocyanin-rich preparations of Vaccinium species (Vaccinium myrtillus, Vaccinium corymbosum, and Vaccinium oxycoccus) as well as a purified glycosylated anthocyanidin were compared. The most potent inhibition of oxidation was observed with V. myrtillus preparation: 50% inhibition with 7 microM of total anthocyanins. This activity was 1.5-4 times higher than that for the other preparations or for the purified anthocyanin. Ascorbate (Vitamin C), at up to 4-fold higher concentrations, did not result in significant inhibition in this assay. Antioxidant activity in the assay correlated strongly (r2>0.91, PVaccinium content of anthocyanins and total cyanidins, but not quercetin or myricetin. The results provide evidence for the high potency of anthocyanins towards a potentially neurotoxic reaction, and provide a basis

  7. Dietary Flavonoids and Gastric Cancer Risk in a Korean Population

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    Hae Dong Woo

    2014-11-01

    Full Text Available Gastric cancer is the most common cancer among men in Korea, and dietary factors are closely associated with gastric cancer risk. We performed a case-control study using 334 cases and 334 matched controls aged 35–75 years. Significant associations were observed in total dietary flavonoids and their subclasses, with the exception of anthocyanidins and isoflavones (OR (95% CI: 0.49 (0.31–0.76, p trend = 0.007 for total flavonoids. However, these associations were not significant after further adjustment for fruits and vegetable consumption (OR (95% CI: 0.62 (0.36–1.09, p trend = 0.458 for total flavonoids. Total flavonoids and their subclasses, except for isoflavones, were significantly associated with a reduced risk gastric cancer in women (OR (95% CI: 0.33 (0.15–0.73, p trend = 0.001 for total flavonoids but not in men (OR (95% CI: 0.70 (0.39–1.24, p trend = 0.393 for total flavonoids. A significant inverse association with gastric cancer risk was observed in flavones, even after additional adjustment for fruits and vegetable consumption in women. No significantly different effects of flavonoids were observed between H. pylori-positive and negative subjects. In conclusion, dietary flavonoids were inversely associated with gastric cancer risk, and these protective effects of dietary flavonoids were prominent in women. No clear differences were observed in the subgroup analysis of H. pylori and smoking status.

  8. Temporal and spatial regulation of anthocyanin biosynthesis provide diverse flower colour intensities and patterning in Cymbidium orchid.

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    Wang, Lei; Albert, Nick W; Zhang, Huaibi; Arathoon, Steve; Boase, Murray R; Ngo, Hanh; Schwinn, Kathy E; Davies, Kevin M; Lewis, David H

    2014-11-01

    This study confirmed pigment profiles in different colour groups, isolated key anthocyanin biosynthetic genes and established a basis to examine the regulation of colour patterning in flowers of Cymbidium orchid. Cymbidium orchid (Cymbidium hybrida) has a range of flower colours, often classified into four colour groups; pink, white, yellow and green. In this study, the biochemical and molecular basis for the different colour types was investigated, and genes involved in flavonoid/anthocyanin synthesis were identified and characterised. Pigment analysis across selected cultivars confirmed cyanidin 3-O-rutinoside and peonidin 3-O-rutinoside as the major anthocyanins detected; the flavonols quercetin and kaempferol rutinoside and robinoside were also present in petal tissue. β-carotene was the major carotenoid in the yellow cultivars, whilst pheophytins were the major chlorophyll pigments in the green cultivars. Anthocyanin pigments were important across all eight cultivars because anthocyanin accumulated in the flower labellum, even if not in the other petals/sepals. Genes encoding the flavonoid biosynthetic pathway enzymes chalcone synthase, flavonol synthase, flavonoid 3' hydroxylase (F3'H), dihydroflavonol 4-reductase (DFR) and anthocyanidin synthase (ANS) were isolated from petal tissue of a Cymbidium cultivar. Expression of these flavonoid genes was monitored across flower bud development in each cultivar, confirming that DFR and ANS were only expressed in tissues where anthocyanin accumulated. Phylogenetic analysis suggested a cytochrome P450 sequence as that of the Cymbidium F3'H, consistent with the accumulation of di-hydroxylated anthocyanins and flavonols in flower tissue. A separate polyketide synthase, identified as a bibenzyl synthase, was isolated from petal tissue but was not associated with pigment accumulation. Our analyses show the diversity in flower colour of Cymbidium orchid derives not from different individual pigments but from subtle

  9. Sicilian pistachio (Pistacia vera L.) nut inhibits expression and release of inflammatory mediators and reverts the increase of paracellular permeability in IL-1β-exposed human intestinal epithelial cells.

    Science.gov (United States)

    Gentile, C; Perrone, A; Attanzio, A; Tesoriere, L; Livrea, M A

    2015-08-01

    Dietary approaches to control inflammatory bowel diseases (IBD) may include proanthocyanidin-rich foods. Our previous research showed that a hydrophilic extract from Sicilian pistachio nut (HPE) contains substantial amounts of proanthocyanidins and possesses anti-inflammatory activities. We studied the effects of HPE and of its polymeric proanthocyanidin fraction (PPF) in a cell model that simulated some conditions of IBD, consisting of interleukin (IL)-1β-stimulated Caco-2 cells. HPE was prepared by Pistacia vera L. nuts, and PPF was isolated from HPE by adsorbance chromatography. Proanthocyanidins were quantified as anthocyanidins after acidic hydrolysis. Differentiated Caco-2 cells were pre-incubated with HPE or PPF and then were exposed to IL-1β. Cell viability and parameters associated with nuclear factor-κB (NF-κB) activation were assayed. Adsorption of polymeric proanthocyanidins to the cell membrane was investigated by transepithelial electrical resistance (TEER) measurements. HPE decreased prostaglandin (PG)E2 production, IL-6 and IL-8 release, and cyclooxygenase (COX)-2 expression. HPE also inhibited the increase in paracellular permeability and reduced NF-κB activation. Polymeric proanthocyanidins, tested at a concentration comparable with their content in HPE, produced effects comparable to HPE. Finally, cell exposure to PPF increases TEER of the epithelial monolayers. Our results provide evidence that pistachio nut components inhibit inflammatory response of intestinal epithelial cells in vitro and indicate polymeric proanthocyanidins as the major bioactive nut components. The protection implies inhibition of NF-κB activation and occurs in parallel with the adsorption of polymeric proanthocyanidins to cell membrane. Our findings suggest that intake of small amounts of pistachio nut can exert beneficial effects to gastrointestinal pathophysiology.

  10. Polymeric proanthocyanidins from Sicilian pistachio (Pistacia vera L.) nut extract inhibit lipopolysaccharide-induced inflammatory response in RAW 264.7 cells.

    Science.gov (United States)

    Gentile, C; Allegra, M; Angileri, F; Pintaudi, A M; Livrea, M A; Tesoriere, L

    2012-04-01

    Positive effects of pistachio nut consumption on plasma inflammatory biomarkers have been described; however, little is known about molecular events associated with these effects. We studied the anti-inflammatory activity of a hydrophilic extract from Sicilian Pistacia L. (HPE) in a macrophage model and investigated bioactive components relevant to the observed effects. HPE oligomer/polymer proanthocyanidin fractions were isolated by adsorbance chromatography, and components quantified as anthocyanidins after acidic hydrolysis. Isoflavones were measured by gradient elution HPLC analysis. RAW 264.7 murine macrophages were pre-incubated with either HPE (1- to 20-mg fresh nut equivalents) or its isolated components for 1 h, then washed before stimulating with lipopolysaccharide (LPS) for 24 h. Cell viability and parameters associated with Nuclear Factor-κB (NF-κB) activation were assayed according to established methods including ELISA, Western blot, or cytofluorimetric analysis. HPE suppressed nitric oxide (NO) and tumor necrosis factor-α (TNF-α) production and inducible NO-synthase levels dose dependently, whereas inhibited prostaglandin E2 (PGE2) release and decreased cyclo-oxygenase-2 content, the lower the HPE amount the higher the effect. Cytotoxic effects were not observed. HPE also caused a dose-dependent decrease in intracellular reactive oxygen species and interfered with the NF-κB activation. Polymeric proanthocyanidins, but not isoflavones, at a concentration comparable with their content in HPE, inhibited NO, PGE2, and TNF-α formation, as well as activation of IκB-α. Oligomeric proanthocyanidins showed only minor effects. Our results provide molecular evidence of anti-inflammatory activity of pistachio nut and indicate polymeric proanthocyanidins as the bioactive components. The mechanism may involve the redox-sensitive transcription factor NF-κB. Potential effects associated with pistachio nut consumption are discussed in terms of the

  11. Red Anthocyanins and Yellow Carotenoids Form the Color of Orange-Flower Gentian (Gentiana lutea L. var. aurantiaca)

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    Gómez Gómez, Lourdes; Veiga, Tania; Ni, Xiuzhen; Farré, Gemma; Capell, Teresa; Guitián, Javier; Guitián, Pablo; Sandmann, Gerhard; Christou, Paul

    2016-01-01

    Flower color is an important characteristic that determines the commercial value of ornamental plants. Gentian flowers occur in a limited range of colors because this species is not widely cultivated as a cut flower. Gentiana lutea L. var. aurantiaca (abbr, aurantiaca) is characterized by its orange flowers, but the specific pigments responsible for this coloration are unknown. We therefore investigated the carotenoid and flavonoid composition of petals during flower development in the orange-flowered gentian variety of aurantiaca and the yellow-flowered variety of G. lutea L. var. lutea (abbr, lutea). We observed minor varietal differences in the concentration of carotenoids at the early and final stages, but only aurantiaca petals accumulated pelargonidin glycosides, whereas these compounds were not found in lutea petals. We cloned and sequenced the anthocyanin biosynthetic gene fragments from petals, and analyzed the expression of these genes in the petals of both varieties to determine the molecular mechanisms responsible for the differences in petal color. Comparisons of deduced amino acid sequences encoded by the isolated anthocyanin cDNA fragments indicated that chalcone synthase (CHS), chalcone isomerase (CHI), anthocyanidin synthase 1 (ANS1) and ANS2 are identical in both aurantiaca and lutea varieties whereas minor amino acid differences of the deduced flavonone 3-hydroxylase (F3H) and dihydroflavonol 4-reductase (DFR) between both varieties were observed. The aurantiaca petals expressed substantially higher levels of transcripts representing CHS, F3H, DFR, ANS and UDP-glucose:flavonoid-3-O-glucosyltransferase genes, compared to lutea petals. Pelargonidin glycoside synthesis in aurantiaca petals therefore appears to reflect the higher steady-state levels of pelargonidin synthesis transcripts. Moreover, possible changes in the substrate specificity of DFR enzymes may represent additional mechanisms for producing red pelargonidin glycosides in petals of

  12. Red Anthocyanins and Yellow Carotenoids Form the Color of Orange-Flower Gentian (Gentiana lutea L. var. aurantiaca.

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    Judit Berman

    Full Text Available Flower color is an important characteristic that determines the commercial value of ornamental plants. Gentian flowers occur in a limited range of colors because this species is not widely cultivated as a cut flower. Gentiana lutea L. var. aurantiaca (abbr, aurantiaca is characterized by its orange flowers, but the specific pigments responsible for this coloration are unknown. We therefore investigated the carotenoid and flavonoid composition of petals during flower development in the orange-flowered gentian variety of aurantiaca and the yellow-flowered variety of G. lutea L. var. lutea (abbr, lutea. We observed minor varietal differences in the concentration of carotenoids at the early and final stages, but only aurantiaca petals accumulated pelargonidin glycosides, whereas these compounds were not found in lutea petals. We cloned and sequenced the anthocyanin biosynthetic gene fragments from petals, and analyzed the expression of these genes in the petals of both varieties to determine the molecular mechanisms responsible for the differences in petal color. Comparisons of deduced amino acid sequences encoded by the isolated anthocyanin cDNA fragments indicated that chalcone synthase (CHS, chalcone isomerase (CHI, anthocyanidin synthase 1 (ANS1 and ANS2 are identical in both aurantiaca and lutea varieties whereas minor amino acid differences of the deduced flavonone 3-hydroxylase (F3H and dihydroflavonol 4-reductase (DFR between both varieties were observed. The aurantiaca petals expressed substantially higher levels of transcripts representing CHS, F3H, DFR, ANS and UDP-glucose:flavonoid-3-O-glucosyltransferase genes, compared to lutea petals. Pelargonidin glycoside synthesis in aurantiaca petals therefore appears to reflect the higher steady-state levels of pelargonidin synthesis transcripts. Moreover, possible changes in the substrate specificity of DFR enzymes may represent additional mechanisms for producing red pelargonidin glycosides in

  13. Silencing of flavanone-3-hydroxylase in apple (Malus × domestica Borkh.) leads to accumulation of flavanones, but not to reduced fire blight susceptibility.

    Science.gov (United States)

    Flachowsky, Henryk; Halbwirth, Heidi; Treutter, Dieter; Richter, Klaus; Hanke, Magda-Viola; Szankowski, Iris; Gosch, Christian; Stich, Karl; Fischer, Thilo C

    2012-02-01

    Transgenic antisense flavanone-3-hydroxylase apple plants were produced to mimic the effect of the agrochemical prohexadione-Ca on apple leaves. This enzyme inhibitor for 2-oxoglutarate dependent dioxygenases is used as a growth retardant and for control of secondary fire blight of leaves. Like using the agent, silencing of flavanone-3-hydroxylase leads to an accumulation of flavanones in leaves, but in contrast not to the formation of 3-deoxyflavonoids. In prohexadione-Ca treated leaves the 3-deoxyflavonoid luteoforol is formed from accumulating flavanones, acting as an antimicrobial compound against the fire blight pathogen Erwinia amylovora. Seemingly, the silencing of just one of the 2-oxoglutarate dependent dioxygenases (in apple also flavonol synthase and anthocyanidin synthase take part downstream in the pathway) does not provide a sufficiently high ratio of flavanones to dihydroflavonols. This seems to be needed to let the dihydroflavonol-4-reductase/flavanone-4-reductase enzyme reduce flavanones to luteoforol, and to let this be reduced by the leucoanthocyanidin-4-reductase/3-deoxyleucoanthocyanidin-4-reductase, each acting with their respective weak secondary activities. Accordingly, also the intended inducible resistance to fire blight by prohexadione-Ca is not observed with the antisense flavanone-3-hydroxylase apple plants. On the other hand, for most transgenic lines with strong flavanone-4-reductase down-regulation, up-regulation of gene expression for the other flavonoid genes was found. This provides further evidence for the feedback regulation of flavonoid gene expression having been previously reported for the prohexadione-Ca inhibited apple plants. Copyright © 2011 Elsevier Masson SAS. All rights reserved.

  14. Promotion of flavonoid biosynthesis in leaves and calli of ornamental crabapple (Malus sp.) by high carbon to nitrogen ratios.

    Science.gov (United States)

    Wan, Huihua; Zhang, Jie; Song, Tingting; Tian, Ji; Yao, Yuncong

    2015-01-01

    Flavonoids are secondary metabolites that play important roles in plant physiology. Despite numerous studies examined the effects of available carbon (C) or nitrogen (N) on flavonoid biosynthesis, the mechanism of C/N interactive effects on flavonoid metabolism is still unclear. In this study, we analyzed the composition of flavonoids and the expression levels of flavonoid-related genes in leaves and calli of crabapple (Malus sp.) cultivars with different leaf colors grown on media with different C/N ratios. Our results show that high C/N ratios induce anthocyanin pigmentation in leaves of the ever-red cultivar 'Royalty' and the spring-red cultivar 'Prairifire,' as well as in three types of calli derived from the ever-green cultivar 'Spring Snow,' but not in the leaves of the ever-green cultivar 'Flame.' This phenomenon therefore correlated with anthocyanin content in these different samples. In addition, high C/N ratios in the growth media resulted in an increase in the concentration of flavones and flavonols in the leaves of the three crabapple cultivars. The transcript levels of the general flavonoid pathway genes [from chalcone synthase (CHS) to uridine diphosphat-glucose: flavonoid 3-O-glycosyltransferase (UFGT) and flavonol synthase (FLS)] increased in response to high C/N ratios, and this in turn was correlated with the concentration of anthocyanins, flavones and flavonols in the leaves and calli. Expression of the late flavonoid/anthocyanin biosynthetic genes, anthocyanidin synthase (ANS), UFGT and FLS in particular, was more strongly influenced by C/N ratios than other structural genes, and the increased expression of the structural genes under high C/N ratios coincided with a coordinated increase in transcript levels of a MYB transcription factor, MYB10. These results are likely to be useful for future generation of plants with an optimized flavonoid/anthocyanin content or desirable organ coloration.

  15. Effect of Arrabidaea chica extracts on the Ehrlich solid tumor development

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    Ana Flávia C. Ribeiro

    2012-04-01

    Full Text Available The aim of this study was to investigate the effect of Arrabidaea chica (Humb. & Bonpl. B. Verl., Bignoniaceae, extracts on Ehrlich solid tumor development in Swiss mice. Leaves of A. chica were extracted with two distinct solvents, ethanol and water. The phytochemical analysis of the extracts indicated different classes of secondary metabolites like as anthocyanidins, flavonoids, tannins and saponins. Ethanol (EE and aqueous (AE extracts at 30 mg/kg reduced the development of Ehrlich solid tumor after ten days of oral treatment. The EE group presented increase in neutrophil count, α1 and β globulin values, and decrease of α2 globulin values. Furthermore, EE reduced the percentage of CD4+ T cells in blood but did not alter the percentage of inflammatory mononuclear cells associated with tumor suggesting a direct action of EE on tumor cells. Reduced tumor development observed in AE group was accompanied by a lower percentage of CD4+ T lymphocytes in blood. At the tumor microenvironment, this treatment decreased the percentage of CD3+ T cells, especially due to a reduction of CD8+ T subpopulation and NK cells. The antitumor activity presented by the AE is possibly related to an anti-inflammatory activity. None of the extracts produced toxic effects in animals. In conclusion, the ethanol and aqueous extracts of A. chica have immunomodulatory and antitumor activities attributed to the presence of flavonoids, such as kaempferol. These effects appear to be related to different mechanisms of action for each extract. This study demonstrates the potential of A. chica as an antitumor agent confirming its use in traditional popular medicine.

  16. Putative Role of Red Wine Polyphenols against Brain Pathology in Alzheimer’s and Parkinson’s Disease

    Science.gov (United States)

    Caruana, Mario; Cauchi, Ruben; Vassallo, Neville

    2016-01-01

    Alzheimer’s disease (AD) and Parkinson’s disease (PD) are the most common age-related neurodegenerative disorders and hence pose remarkable socio-economical burdens to both families and state. Although AD and PD have different clinical and neuropathological features, they share common molecular mechanisms that appear to be triggered by multi-factorial events, such as protein aggregation, mitochondrial dysfunction, oxidative stress (OS), and neuroinflammation, ultimately leading to neuronal cell death. Currently, there are no established and validated disease-modifying strategies for either AD or PD. Among the various lifestyle factors that may prevent or slow age-related neurodegenerative diseases, epidemiological studies on moderate consumption of red wine, especially as part of a holistic Mediterranean diet, have attracted increasing interest. Red wine is particularly rich in specific polyphenolic compounds that appear to affect the biological processes of AD and PD, such as quercetin, myricetin, catechins, tannins, anthocyanidins, resveratrol, and ferulic acid. Indeed, there is now a consistent body of in vitro and in vivo data on the neuroprotective effects of red wine polyphenols (RWP) showing that they do not merely possess antioxidant properties, but may additionally act upon, in a multi-target manner, the underlying key mechanisms featuring in both AD and PD. Furthermore, it is important that bioavailability issues are addressed in order for neuroprotection to be relevant in a clinical study scenario. This review summarizes the current knowledge about the major classes of RWP and places into perspective their potential to be considered as nutraceuticals to target neuropathology in AD and PD. PMID:27570766

  17. Putative role of red wine polyphenols against brain pathology in Alzheimer’s and Parkinson’s disease

    Directory of Open Access Journals (Sweden)

    Mario Caruana

    2016-08-01

    Full Text Available Alzheimer’s disease (AD and Parkinson’s disease (PD are the most common age-related neurodegenerative disorders and hence pose remarkable socio-economical burdens to both families and state. Although AD and PD have different clinical and neuropathological features, they share common molecular mechanisms which appear to be triggered by multi-factorial events such as protein aggregation, mitochondrial dysfunction, oxidative stress (OS and neuroinflammation, ultimately leading to neuronal cell death. Currently, there are no established and validated disease-modifying strategies for either AD or PD. Among the various lifestyle factors that may prevent or slow age-related neurodegenerative diseases, epidemiological studies on moderate consumption of red wine, especially as part of a holistic Mediterranean diet, have attracted increasing interest. Red wine is particularly rich in specific polyphenolic compounds which appear to affect the biological processes of AD and PD, such as quercetin, myricetin, catechins, tannins, anthocyanidins, resveratrol and ferulic acid. Indeed, there is now a consistent body of in vitro and in vivo data on the neuroprotective effects of red wine polyphenols showing that they do not merely possess anti-oxidant properties, but may additionally act upon, in a multi-target manner, the underlying key mechanisms featuring in both AD and PD. Further, it is important that bioavailability issues are addressed in order for neuroprotection to be relevant in a clinical study scenario. This review summarises the current knowledge about the major classes of red wine polyphenols and places into perspective their potential to be considered as nutraceuticals to target neuropathology in AD and PD.

  18. Putative Role of Red Wine Polyphenols against Brain Pathology in Alzheimer's and Parkinson's Disease.

    Science.gov (United States)

    Caruana, Mario; Cauchi, Ruben; Vassallo, Neville

    2016-01-01

    Alzheimer's disease (AD) and Parkinson's disease (PD) are the most common age-related neurodegenerative disorders and hence pose remarkable socio-economical burdens to both families and state. Although AD and PD have different clinical and neuropathological features, they share common molecular mechanisms that appear to be triggered by multi-factorial events, such as protein aggregation, mitochondrial dysfunction, oxidative stress (OS), and neuroinflammation, ultimately leading to neuronal cell death. Currently, there are no established and validated disease-modifying strategies for either AD or PD. Among the various lifestyle factors that may prevent or slow age-related neurodegenerative diseases, epidemiological studies on moderate consumption of red wine, especially as part of a holistic Mediterranean diet, have attracted increasing interest. Red wine is particularly rich in specific polyphenolic compounds that appear to affect the biological processes of AD and PD, such as quercetin, myricetin, catechins, tannins, anthocyanidins, resveratrol, and ferulic acid. Indeed, there is now a consistent body of in vitro and in vivo data on the neuroprotective effects of red wine polyphenols (RWP) showing that they do not merely possess antioxidant properties, but may additionally act upon, in a multi-target manner, the underlying key mechanisms featuring in both AD and PD. Furthermore, it is important that bioavailability issues are addressed in order for neuroprotection to be relevant in a clinical study scenario. This review summarizes the current knowledge about the major classes of RWP and places into perspective their potential to be considered as nutraceuticals to target neuropathology in AD and PD.

  19. Transcriptome analysis and anthocyanin-related genes in red leaf lettuce.

    Science.gov (United States)

    Zhang, Y Z; Xu, S Z; Cheng, Y W; Ya, H Y; Han, J M

    2016-01-29

    This study aimed to analyze the transcriptome profile of red lettuce and identify the genes involved in anthocyanin accumulation. Red leaf lettuce is a popular vegetable and popular due to its high anthocyanin content. However, there is limited information available about the genes involved in anthocyanin biosynthesis in this species. In this study, transcriptomes of 15-day-old seedlings and 40-day-old red lettuce leaves were analyzed using an Illuminia HiseqTM 2500 platform. A total of 10.6 GB clean data were obtained and de novo assembled into 83,333 unigenes with an N50 of 1067. After annotation against public databases, 51,850 unigene sequences were identified, among which 46,087 were annotated in the NCBI non-redundant protein database, and 41,752 were annotated in the Swiss-Prot database. A total of 9125 unigenes were mapped into 163 pathways using the Kyoto Encyclopedia of Genes and Genomes database. Thirty-four structural genes were found to cover the main steps of the anthocyanin pathway, including chalcone synthase, chalcone isomerase, flavanone 3-hydroxylase, flavonoid 3'-hydroxylase, flavonoid 3',5'-hydroxylase, dihydroflavonol 4-reductase, and anthocyanidin synthase. Seven MYB, three bHLH, and two WD40 genes, considered anthocyanin regulatory genes, were also identified. In addition, 3607 simple sequence repeat (SSR) markers were identified from 2916 unigenes. This research uncovered the transcriptomic characteristics of red leaf lettuce seedlings and mature plants. The identified candidate genes related to anthocyanin biosynthesis and the detected SSRs provide useful tools for future molecular breeding studies.

  20. Inhibition on cholinesterase and tyrosinase by alkaloids and phenolics from Aristotelia chilensis leaves.

    Science.gov (United States)

    Cespedes, Carlos L; Balbontin, Cristian; Avila, Jose G; Dominguez, Mariana; Alarcon, Julio; Paz, Cristian; Burgos, Viviana; Ortiz, Leandro; Peñaloza-Castro, Ignacio; Seigler, David S; Kubo, Isao

    2017-11-01

    It is reported in this study the effect of isolates from leaves of Aristotelia chilensis as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and tyrosinase enzymes. The aim of the paper was to evaluate the activity of A. chilensis towards different enzymes. In addition to pure compounds, extracts rich in alkaloids and phenolics were tested. The most active F5 inhibited AChE (79.5% and 89.8% at 10.0 and 20.0 μg/mL) and against BChE (89.5% and 97.8% at 10.0 and 20.0 μg/mL), showing a strong mixed-type inhibition against AChE and BChE. F3 (a mixture of flavonoids and phenolics acids), showed IC 50 of 90.7 and 59.6 μg/mL of inhibitory activity against AChE and BChE, inhibiting the acetylcholinesterase competitively. Additionally, F3 showed and high potency as tyrosinase inhibitor with IC 50 at 8.4 μg/mL. Sample F4 (anthocyanidins and phenolic composition) presented a complex, mixed-type inhibition of tyrosinase with a IC 50 of 39.8 μg/mL. The findings in this investigation show that this natural resource has a strong potential for future research in the search of new phytotherapeutic treatments for cholinergic deterioration ailments avoiding the side effects of synthetic drugs. This is the first report as cholinesterases and tyrosinase inhibitors of alkaloids and phenolics from A. chilensis leaves. Copyright © 2017 Elsevier Ltd. All rights reserved.

  1. Ectopic Expression of the Grape Hyacinth (Muscari armeniacum R2R3-MYB Transcription Factor Gene, MaAN2, Induces Anthocyanin Accumulation in Tobacco

    Directory of Open Access Journals (Sweden)

    Kaili Chen

    2017-06-01

    Full Text Available Anthocyanins are responsible for the different colors of ornamental plants. Grape hyacinth (Muscari armeniacum, a monocot plant with bulbous flowers, is popular for its fascinating blue color. In the present study, we functionally characterized an R2R3-MYB transcription factor gene MaAN2 from M. armeniacum. Our results indicated that MaAN2 participates in controlling anthocyanin biosynthesis. Sequence alignment and phylogenetic analysis suggested that MaAN2 belonged to the R2R3-MYB family AN2 subgroup. The anthocyanin accumulation of grape hyacinth flowers was positively correlated with the expression of MaAN2. And the transcriptional expression of MaAN2 was also consistent with that of M. armeniacum dihydroflavonol 4-reductase (MaDFR and M. armeniacum anthocyanidin synthase (MaANS in flowers. A dual luciferase transient expression assay indicated that when MaAN2 was co-inflitrated with Arabidopsis thaliana TRANSPARENT TESTA8 (AtTT8, it strongly activated the promoters of MaDFR and MaANS, but not the promoters of M. armeniacum chalcone synthase (MaCHS, M. armeniacum chalcone isomerase (MaCHI, and M. armeniacum flavanone 3-hydroxylase (MaF3H. Bimolecular fluorescence complementation assay confirmed that MaAN2 interacted with AtTT8 in vivo. The ectopic expression of MaAN2 in Nicotiana tabacum resulted in obvious red coloration of the leaves and much redder flowers. Almost all anthocyanin biosynthetic genes were remarkably upregulated in the leaves and flowers of the transgenic tobacco, and NtAn1a and NtAn1b (two basic helix–loop–helix anthocyanin regulatory genes were highly expressed in the transformed leaves, compared to the empty vector transformants. Collectively, our results suggest that MaAN2 plays a role in anthocyanin biosynthesis.

  2. Promotion of flavonoid biosynthesis in leaves and calli of ornamental crabapple (Malus spp. by high carbon to nitrogen ratios

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    Huihua eWan

    2015-09-01

    Full Text Available Flavonoids are secondary metabolites that play important roles in plant physiology. Despite numerous studies examined the effects of available carbon (C or nitrogen (N on flavonoid biosynthesis, the mechanism of C/N interactive effects on flavonoid metabolism is still unclear. In this study, we analyzed the composition of flavonoids and the expression levels of flavonoid-related genes in leaves and calli of crabapple (Malus spp. cultivars with different leaf colors grown on media with different C/N ratios. Our results show that high C/N ratios induce anthocyanin pigmentation in leaves of the ever-red cultivar ‘Royalty’ and the spring-red cultivar ‘Prairifire’, as well as in three types of calli derived from the ever-green cultivar ‘Spring Snow’, but not in the leaves of the ever-green cultivar ‘Flame’. This phenomenon therefore correlated with anthocyanin content in these different samples. In addition, high C/N ratios in the growth media resulted in an increase in the concentration of flavones and flavonols in the leaves of the three crabapple cultivars. The transcript levels of the general flavonoid pathway genes [from chalcone synthase (CHS to uridine diphosphate (UDP-glucose: flavonoid 3-O-glycosyltransferase (UFGT and flavonol synthase (FLS] increased in response to high C/N ratios, and this in turn was correlated with the concentration of anthocyanin, flavone and flavonol in the leaves and calli. Expression of the late flavonoid/anthocyanin biosynthetic genes, anthocyanidin synthase (ANS, UFGT and FLS in particular, was more strongly influenced by C/N ratios than other structural genes, and the increased expression of the structural genes under high C/N ratios coincided with a coordinated increase in transcript levels of a MYB transcription factor, MYB10. These results are likely to be useful for future generation of plants with an optimized flavonoid/anthocyanin content or desirable organ coloration.

  3. Post-transcriptional silencing of flavonol synthase mRNA in tobacco leads to fruits with arrested seed set.

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    Monika Mahajan

    Full Text Available Flavonoids are synthesized by phenylpropanoid pathway. They are known to participate in large number of physiological and biochemical processes in plants. Parthenocarpy and male sterility has earlier been reported by silencing chalcone synthase (CHS encoding gene. Silencing of CHS has blocked the synthesis of most of useful flavonoids including flavan-3-ols and flavonols. Also, these studies could not identify whether parthenocarpy/male sterility were due to lack of flavan-3-ols or flavonols or both. Flavonol synthase (FLS is an important enzyme of flavonoid pathway that catalyzes the formation of flavonols. In this article, we propose a novel strategy towards the generation of seedless or less-seeded fruits by downregulation of flavonol biosynthesis in tobacco (Nicotiana tabacum cv Xanthi through post-transcriptional gene silencing (PTGS of FLS encoding mRNA. The FLS silenced lines were observed for 20-80% reduction in FLS encoding gene expression and 25-93% reduction in flavonol (quercetin content. Interestingly, these FLS silenced tobacco lines also showed reduction in their anthocyanidins content. While the content of flavan-3-ols (catechin, epi-catechin and epi-gallocatechin was found to be increased in FLS silenced lines. The delayed flowering in FLS silenced lines could be due to decrease in level of indole acetic acid (IAA at apical region of their shoots. Furthermore, the pollen germination was hampered and pollens were unable to produce functional pollen tube in FLS silenced tobacco lines. Pods of FLS silenced lines contained significantly less number of seeds. The in vitro and in vivo studies where 1 µM quercetin was supplied to germination media, documented the restoration of normal pollen germination and pollen tube growth. This finding identified the role of flavonols particularly quercetin in pollen germination as well as in the regulation of plant fertility. Results also suggest a novel approach towards generation of seedless

  4. Cultivar Variation in Hormonal Balance Is a Significant Determinant of Disease Susceptibility to Xanthomonas campestris pv. campestris in Brassica napus

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    Md. Tabibul Islam

    2017-12-01

    Full Text Available This study aimed to directly elucidate cultivar variation in disease susceptibility and disease responses in relation to hormonal status in the interaction of Brassica napus cultivars and Xanthomonas campestris pv. campestris (Xcc, the causal agent of black rot disease. Fully expanded leaves of six B. napus cultivars (cvs. Capitol, Youngsan, Saturnin, Colosse, Tamra, and Mosa were inoculated with Xcc. At 14 days post-inoculation with Xcc, cultivar variation in susceptibility or resistance was interpreted with defense responses as estimated by redox status, defensive metabolites, and expression of phenylpropanoid synthesis-related genes in relation to endogenous hormonal status. Disease susceptibility of six cultivars was distinguished by necrotic lesions in the Xcc-inoculated leaves and characterized concurrently based on the higher increase in reactive oxygen species and lipid peroxidation. Among these cultivars, as the susceptibility was higher, the ratios of abscisic acid (ABA/jasmonic acid (JA and salicylic acid (SA/JA tended to increase with enhanced expression of SA signaling regulatory gene NPR1 and transcriptional factor TGA1 and antagonistic suppression of JA-regulated gene PDF 1.2. In the resistant cultivar (cv. Capitol, accumulation of defensive metabolites with enhanced expression of genes involved in flavonoids (chalcone synthase, proanthocyanidins (anthocyanidin reductase, and hydroxycinnamic acids (ferulate-5-hydroxylase biosynthesis and higher redox status were observed, whereas the opposite results were obtained for susceptible cultivars (cvs. Mosa and Tamra. These results clearly indicate that cultivar variation in susceptibility to infection by Xcc was determined by enhanced alteration of the SA/JA ratio, as a negative regulator of redox status and phenylpropanoid synthesis in the Brasica napus–Xcc pathosystem.

  5. A de novo transcriptomic approach to identify flavonoids and anthocyanins switch-off in olive (Olea europaea L. drupes at different stages of maturation

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    Domenico eIaria

    2016-01-01

    Full Text Available During ripening, the fruits of the olive tree (Olea europaea L. undergo a progressive chromatic change characterized by the formation of a red-brown spot which gradually extends on the epidermis and in the innermost part of the mesocarp. This event finds an exception in the Leucocarpa cultivar, in which we observe a destabilized equilibrium between the metabolisms of chlorophyll and other pigments, particularly the anthocyanins whose switch-off during maturation promotes the white coloration of fruits. Despite its importance, genomic information on the olive tree is still lacking. Different RNA-seq libraries were generated from drupes of ‘Leucocarpa’ and ‘Cassanese’ olive genotypes, sampled at 100 and 130 days after flowering (DAF, and were used in order to identify transcripts involved in the main phenotypic changes of fruits during maturation and their corresponding expression patterns. A total of 103,359 transcripts were obtained and 3792 and 3064 were differentially expressed in ‘Leucocarpa’ and ‘Cassanese’ genotypes, respectively, during 100-130 DAF transition. Among them flavonoid and anthocyanin related transcripts such as phenylalanine ammonia lyase (PAL, cinnamate 4-hydroxylase (C4H, 4-coumarate-CoA ligase (4CL, chalcone synthase (CHS, chalcone isomerase (CHI, flavanone 3-hydroxylase (F3H, flavonol 3’-hydrogenase (F3'H, flavonol 3’5’-hydrogenase (F3'5'H, flavonol synthase (FLS, dihydroflavonol 4-reductase (DFR, anthocyanidin synthase (ANS, UDP-glucose:anthocianidin:flavonoid glucosyltransferase (UFGT were identified.These results contribute to reducing the current gap in information regarding metabolic processes, including those linked to fruit pigmentation in the olive.

  6. Proanthocyanidin Synthesis in Chinese Bayberry (Myrica rubra Sieb. et Zucc. Fruits

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    Liyu Shi

    2018-02-01

    Full Text Available Proanthocyanidins (PAs are distributed widely in Chinese bayberry fruit and have been associated with human health benefits, but molecular and biochemical characterization of PA biosynthesis remains unclear. Here, two genes encoding key PA biosynthetic enzymes, anthocyanidin reductase (ANR and leucoanthocyanidin reductase (LAR were isolated in bayberry fruit. MrANR was highly expressed at the early stage of fruit development when soluble PAs accumulated at high levels. Meanwhile, the transcript abundance of both MrANR and MrLAR observed at the late stage was paralleled with the high amounts of insoluble PAs. LC-MS/MS showed that PAs in developing Chinese bayberry fruits were comprised predominantly of epigallocatechin-3-O-gallate terminal subunits, while the extension subunits were a mixture of epigallocatechin-3-O-gallate, epigallocatechin and catechin. Recombinant MrANR protein converted cyanidin to a mixture of epicatechin and catechin, and delphinidin to a mixture of epigallocatechin and gallocatechin in vitro. Recombinant MrLAR was active with leucocyanidin as substrate to produce catechin. Ectopic expression of MrANR in tobacco reduced anthocyanin levels but increased PA accumulation. The catechin and epicatechin contents in transgenic flowers overexpressed MrANR were significantly higher than those of wild-type. However, overexpression of MrLAR in tobacco led to an increase in catechin levels but had no impact on PA contents. Quantitative real time PCR revealed that the loss of anthocyanin in transgenic flowers overexpressed MrANR or MrLAR is probably attributed to decreased expression of tobacco chalcone isomerase (CHI gene. Our results not only reveal in vivo and in vitro functions for ANR and LAR but also provide a resource for understanding the mechanism of PA biosynthesis in Chinese bayberry fruit.

  7. Evolution of flavone synthase I from parsley flavanone 3beta-hydroxylase by site-directed mutagenesis.

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    Gebhardt, Yvonne Helen; Witte, Simone; Steuber, Holger; Matern, Ulrich; Martens, Stefan

    2007-07-01

    Flavanone 3beta-hydroxylase (FHT) and flavone synthase I (FNS I) are 2-oxoglutarate-dependent dioxygenases with 80% sequence identity, which catalyze distinct reactions in flavonoid biosynthesis. However, FNS I has been reported exclusively from a few Apiaceae species, whereas FHTs are more abundant. Domain-swapping experiments joining the N terminus of parsley (Petroselinum crispum) FHT with the C terminus of parsley FNS I and vice versa revealed that the C-terminal portion is not essential for FNS I activity. Sequence alignments identified 26 amino acid substitutions conserved in FHT versus FNS I genes. Homology modeling, based on the related anthocyanidin synthase structure, assigned seven of these amino acids (FHT/FNS I, M106T, I115T, V116I, I131F, D195E, V200I, L215V, and K216R) to the active site. Accordingly, FHT was modified by site-directed mutagenesis, creating mutants encoding from one to seven substitutions, which were expressed in yeast (Saccharomyces cerevisiae) for FNS I and FHT assays. The exchange I131F in combination with either M106T and D195E or L215V and K216R replacements was sufficient to confer some FNS I side activity. Introduction of all seven FNS I substitutions into the FHT sequence, however, caused a nearly complete change in enzyme activity from FHT to FNS I. Both FHT and FNS I were proposed to initially withdraw the beta-face-configured hydrogen from carbon-3 of the naringenin substrate. Our results suggest that the 7-fold substitution affects the orientation of the substrate in the active-site pocket such that this is followed by syn-elimination of hydrogen from carbon-2 (FNS I reaction) rather than the rebound hydroxylation of carbon-3 (FHT reaction).

  8. Evolution of Flavone Synthase I from Parsley Flavanone 3β-Hydroxylase by Site-Directed Mutagenesis1[W][OA

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    Gebhardt, Yvonne Helen; Witte, Simone; Steuber, Holger; Matern, Ulrich; Martens, Stefan

    2007-01-01

    Flavanone 3β-hydroxylase (FHT) and flavone synthase I (FNS I) are 2-oxoglutarate-dependent dioxygenases with 80% sequence identity, which catalyze distinct reactions in flavonoid biosynthesis. However, FNS I has been reported exclusively from a few Apiaceae species, whereas FHTs are more abundant. Domain-swapping experiments joining the N terminus of parsley (Petroselinum crispum) FHT with the C terminus of parsley FNS I and vice versa revealed that the C-terminal portion is not essential for FNS I activity. Sequence alignments identified 26 amino acid substitutions conserved in FHT versus FNS I genes. Homology modeling, based on the related anthocyanidin synthase structure, assigned seven of these amino acids (FHT/FNS I, M106T, I115T, V116I, I131F, D195E, V200I, L215V, and K216R) to the active site. Accordingly, FHT was modified by site-directed mutagenesis, creating mutants encoding from one to seven substitutions, which were expressed in yeast (Saccharomyces cerevisiae) for FNS I and FHT assays. The exchange I131F in combination with either M106T and D195E or L215V and K216R replacements was sufficient to confer some FNS I side activity. Introduction of all seven FNS I substitutions into the FHT sequence, however, caused a nearly complete change in enzyme activity from FHT to FNS I. Both FHT and FNS I were proposed to initially withdraw the β-face-configured hydrogen from carbon-3 of the naringenin substrate. Our results suggest that the 7-fold substitution affects the orientation of the substrate in the active-site pocket such that this is followed by syn-elimination of hydrogen from carbon-2 (FNS I reaction) rather than the rebound hydroxylation of carbon-3 (FHT reaction). PMID:17535823

  9. Red Anthocyanins and Yellow Carotenoids Form the Color of Orange-Flower Gentian (Gentiana lutea L. var. aurantiaca).

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    Berman, Judit; Sheng, Yanmin; Gómez Gómez, Lourdes; Veiga, Tania; Ni, Xiuzhen; Farré, Gemma; Capell, Teresa; Guitián, Javier; Guitián, Pablo; Sandmann, Gerhard; Christou, Paul; Zhu, Changfu

    2016-01-01

    Flower color is an important characteristic that determines the commercial value of ornamental plants. Gentian flowers occur in a limited range of colors because this species is not widely cultivated as a cut flower. Gentiana lutea L. var. aurantiaca (abbr, aurantiaca) is characterized by its orange flowers, but the specific pigments responsible for this coloration are unknown. We therefore investigated the carotenoid and flavonoid composition of petals during flower development in the orange-flowered gentian variety of aurantiaca and the yellow-flowered variety of G. lutea L. var. lutea (abbr, lutea). We observed minor varietal differences in the concentration of carotenoids at the early and final stages, but only aurantiaca petals accumulated pelargonidin glycosides, whereas these compounds were not found in lutea petals. We cloned and sequenced the anthocyanin biosynthetic gene fragments from petals, and analyzed the expression of these genes in the petals of both varieties to determine the molecular mechanisms responsible for the differences in petal color. Comparisons of deduced amino acid sequences encoded by the isolated anthocyanin cDNA fragments indicated that chalcone synthase (CHS), chalcone isomerase (CHI), anthocyanidin synthase 1 (ANS1) and ANS2 are identical in both aurantiaca and lutea varieties whereas minor amino acid differences of the deduced flavonone 3-hydroxylase (F3H) and dihydroflavonol 4-reductase (DFR) between both varieties were observed. The aurantiaca petals expressed substantially higher levels of transcripts representing CHS, F3H, DFR, ANS and UDP-glucose:flavonoid-3-O-glucosyltransferase genes, compared to lutea petals. Pelargonidin glycoside synthesis in aurantiaca petals therefore appears to reflect the higher steady-state levels of pelargonidin synthesis transcripts. Moreover, possible changes in the substrate specificity of DFR enzymes may represent additional mechanisms for producing red pelargonidin glycosides in petals of

  10. Functional Characterization of Proanthocyanidin Pathway Enzymes from Tea and Their Application for Metabolic Engineering1[W][OA

    Science.gov (United States)

    Pang, Yongzhen; Abeysinghe, I. Sarath B.; He, Ji; He, Xianzhi; Huhman, David; Mewan, K. Mudith; Sumner, Lloyd W.; Yun, Jianfei; Dixon, Richard A.

    2013-01-01

    Tea (Camellia sinensis) is rich in specialized metabolites, especially polyphenolic proanthocyanidins (PAs) and their precursors. To better understand the PA pathway in tea, we generated a complementary DNA library from leaf tissue of the blister blight-resistant tea cultivar TRI2043 and functionally characterized key enzymes responsible for the biosynthesis of PA precursors. Structural genes encoding enzymes involved in the general phenylpropanoid/flavonoid pathway and the PA-specific branch pathway were well represented in the library. Recombinant tea leucoanthocyanidin reductase (CsLAR) expressed in Escherichia coli was active with leucocyanidin as substrate to produce the 2R,3S-trans-flavan-ol (+)-catechin in vitro. Two genes encoding anthocyanidin reductase, CsANR1 and CsANR2, were also expressed in E. coli, and the recombinant proteins exhibited similar kinetic properties. Both converted cyanidin to a mixture of (+)-epicatechin and (−)-catechin, although in different proportions, indicating that both enzymes possess epimerase activity. These epimers were unexpected based on the belief that tea PAs are made from (−)-epicatechin and (+)-catechin. Ectopic expression of CsANR2 or CsLAR led to the accumulation of low levels of PA precursors and their conjugates in Medicago truncatula hairy roots and anthocyanin-overproducing tobacco (Nicotiana tabacum), but levels of oligomeric PAs were very low. Surprisingly, the expression of CsLAR in tobacco overproducing anthocyanin led to the accumulation of higher levels of epicatechin and its glucoside than of catechin, again highlighting the potential importance of epimerization in flavan-3-ol biosynthesis. These data provide a resource for understanding tea PA biosynthesis and tools for the bioengineering of flavanols. PMID:23288883

  11. Functional characterization of proanthocyanidin pathway enzymes from tea and their application for metabolic engineering.

    Science.gov (United States)

    Pang, Yongzhen; Abeysinghe, I Sarath B; He, Ji; He, Xianzhi; Huhman, David; Mewan, K Mudith; Sumner, Lloyd W; Yun, Jianfei; Dixon, Richard A

    2013-03-01

    Tea (Camellia sinensis) is rich in specialized metabolites, especially polyphenolic proanthocyanidins (PAs) and their precursors. To better understand the PA pathway in tea, we generated a complementary DNA library from leaf tissue of the blister blight-resistant tea cultivar TRI2043 and functionally characterized key enzymes responsible for the biosynthesis of PA precursors. Structural genes encoding enzymes involved in the general phenylpropanoid/flavonoid pathway and the PA-specific branch pathway were well represented in the library. Recombinant tea leucoanthocyanidin reductase (CsLAR) expressed in Escherichia coli was active with leucocyanidin as substrate to produce the 2R,3S-trans-flavan-ol (+)-catechin in vitro. Two genes encoding anthocyanidin reductase, CsANR1 and CsANR2, were also expressed in E. coli, and the recombinant proteins exhibited similar kinetic properties. Both converted cyanidin to a mixture of (+)-epicatechin and (-)-catechin, although in different proportions, indicating that both enzymes possess epimerase activity. These epimers were unexpected based on the belief that tea PAs are made from (-)-epicatechin and (+)-catechin. Ectopic expression of CsANR2 or CsLAR led to the accumulation of low levels of PA precursors and their conjugates in Medicago truncatula hairy roots and anthocyanin-overproducing tobacco (Nicotiana tabacum), but levels of oligomeric PAs were very low. Surprisingly, the expression of CsLAR in tobacco overproducing anthocyanin led to the accumulation of higher levels of epicatechin and its glucoside than of catechin, again highlighting the potential importance of epimerization in flavan-3-ol biosynthesis. These data provide a resource for understanding tea PA biosynthesis and tools for the bioengineering of flavanols.

  12. Estimation of dietary flavonoid intake and major food sources of Korean adults.

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    Jun, Shinyoung; Shin, Sangah; Joung, Hyojee

    2016-02-14

    Epidemiological studies have suggested that flavonoids exhibit preventive effects on degenerative diseases. However, lack of sufficient data on flavonoid intake has limited evaluating the proposed effects in populations. Therefore, we aimed to estimate the total and individual flavonoid intakes among Korean adults and determine the major dietary sources of these flavonoids. We constructed a flavonoid database of common Korean foods, based on the food list reported in the 24-h recall of the Korea National Health and Nutrition Examination Survey (KNHANES) 2007-2012, using data from the Korea Functional Food Composition Table, US Department of Agriculture flavonoid database, Phenol-Explorer database and other analytical studies. This database, which covers 49 % of food items and 76 % of food intake, was linked with the 24-h recall data of 33 581 subjects aged ≥19 years in the KNHANES 2007-2012. The mean daily intake of total flavonoids in Korean adults was 318·0 mg/d, from proanthocyanidins (22·3%), flavonols (20·3%), isoflavones (18·1%), flavan-3-ols (16·2%), anthocyanidins (11·6%), flavanones (11·3%) and flavones (0·3%). The major contributing food groups to the flavonoid intake were fruits (54·4%), vegetables (20·5%), legumes and legume products (16·2%) and beverages and alcohols (3·1%), and the major contributing food items were apples (21·9%), mandarins (12·5%), tofu (11·5%), onions (9·6%) and grapes (9·0%). In the regression analysis, the consumption of legumes and legume products, vegetables and fruits predicted total flavonoid intake the most. The findings of this study could facilitate further investigation on the health benefits of flavonoids and provide the basic information for establishing recommended flavonoid intakes for Koreans.

  13. A "White" Anthocyanin-less Pomegranate (Punica granatum L.) Caused by an Insertion in the Coding Region of the Leucoanthocyanidin Dioxygenase (LDOX; ANS) Gene.

    Science.gov (United States)

    Ben-Simhon, Zohar; Judeinstein, Sylvie; Trainin, Taly; Harel-Beja, Rotem; Bar-Ya'akov, Irit; Borochov-Neori, Hamutal; Holland, Doron

    2015-01-01

    Color is an important determinant of pomegranate fruit quality and commercial value. To understand the genetic factors controlling color in pomegranate, chemical, molecular and genetic characterization of a "white" pomegranate was performed. This unique accession is lacking the typical pomegranate color rendered by anthocyanins in all tissues of the plant, including flowers, fruit (skin and arils) and leaves. Steady-state gene-expression analysis indicated that none of the analyzed "white" pomegranate tissues are able to synthesize mRNA corresponding to the PgLDOX gene (leucoanthocyanidin dioxygenase, also called ANS, anthocyanidin synthase), which is one of the central structural genes in the anthocyanin-biosynthesis pathway. HPLC analysis revealed that none of the "white" pomegranate tissues accumulate anthocyanins, whereas other flavonoids, corresponding to biochemical reactions upstream of LDOX, were present. Molecular analysis of the "white" pomegranate revealed the presence of an insertion and an SNP within the coding region of PgLDOX. It was found that the SNP does not change amino acid sequence and is not fully linked with the "white" phenotype in all pomegranate accessions from the collection. On the other hand, genotyping of pomegranate accessions from the collection and segregating populations for the "white" phenotype demonstrated its complete linkage with the insertion, inherited as a recessive single-gene trait. Taken together, the results indicate that the insertion in PgLDOX is responsible for the "white" anthocyanin-less phenotype. These data provide the first direct molecular, genetic and chemical evidence for the effect of a natural modification in the LDOX gene on color accumulation in a fruit-bearing woody perennial deciduous tree. This modification can be further utilized to elucidate the physiological role of anthocyanins in protecting the tree organs from harmful environmental conditions, such as temperature and UV radiation.

  14. Flavan-3-ols Are an Effective Chemical Defense against Rust Infection.

    Science.gov (United States)

    Ullah, Chhana; Unsicker, Sybille B; Fellenberg, Christin; Constabel, C Peter; Schmidt, Axel; Gershenzon, Jonathan; Hammerbacher, Almuth

    2017-12-01

    Phenolic secondary metabolites are often thought to protect plants against attack by microbes, but their role in defense against pathogen infection in woody plants has not been investigated comprehensively. We studied the biosynthesis, occurrence, and antifungal activity of flavan-3-ols in black poplar ( Populus nigra ), which include both monomers, such as catechin, and oligomers, known as proanthocyanidins (PAs). We identified and biochemically characterized three leucoanthocyanidin reductases and two anthocyanidin reductases from P. nigra involved in catalyzing the last steps of flavan-3-ol biosynthesis, leading to the formation of catechin [2,3-trans-(+)-flavan-3-ol] and epicatechin [2,3-cis-(-)-flavan-3-ol], respectively. Poplar trees that were inoculated with the biotrophic rust fungus ( Melampsora larici-populina ) accumulated higher amounts of catechin and PAs than uninfected trees. The de novo-synthesized catechin and PAs in the rust-infected poplar leaves accumulated significantly at the site of fungal infection in the lower epidermis. In planta concentrations of these compounds strongly inhibited rust spore germination and reduced hyphal growth. Poplar genotypes with constitutively higher levels of catechin and PAs as well as hybrid aspen ( Populus tremula × Populus alba ) overexpressing the MYB134 transcription factor were more resistant to rust infection. Silencing PnMYB134 , on the other hand, decreased flavan-3-ol biosynthesis and increased susceptibility to rust infection. Taken together, our data indicate that catechin and PAs are effective antifungal defenses in poplar against foliar rust infection. © 2017 American Society of Plant Biologists. All Rights Reserved.

  15. Expression Differences of Pigment Structural Genes and Transcription Factors Explain Flesh Coloration in Three Contrasting Kiwifruit Cultivars

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    Yanfei Liu

    2017-09-01

    Full Text Available Fruits of kiwifruit cultivars (Actinidia chinensis and A. deliciosa generally have green or yellow flesh when ripe. A small number of genotypes have red flesh but this coloration is usually restricted to the inner pericarp. Three kiwifruit cultivars having red (‘Hongyang’, or yellow (‘Jinnong-2’, or green (‘Hayward’ flesh were investigated for their color characteristics and pigment contents during development and ripening. The results show the yellow of the ‘Jinnong-2’ fruit is due to the combined effects of chlorophyll degradation and of beta-carotene accumulation. The red inner pericarps of ‘Hongyang’ fruit are due to anthocyanin accumulation. Expression differences of the pathway genes in the inner pericarps of the three different kiwifruits suggest that stay-green (SGR controls the degradation of chlorophylls, while lycopene beta-cyclase (LCY-β controls the biosynthesis of beta-carotene. The abundance of anthocyanin in the inner pericarps of the ‘Hongyang’ fruit is the results of high expressions of UDP flavonoid glycosyltransferases (UFGT. At the same time, expressions of anthocyanin transcription factors show that AcMYBF110 expression parallels changes in anthocyanin concentration, so seems to be a key R2R3 MYB, regulating anthocyanin biosynthesis. Further, transient color assays reveal that AcMYBF110 can autonomously induce anthocyanin accumulation in Nicotiana tabacum leaves by activating the transcription of dihydroflavonol 4-reductase (NtDFR, anthocyanidin synthase (NtANS and NtUFGT. For basic helix-loop-helix proteins (bHLHs and WD-repeat proteins (WD40s, expression differences show these may depend on AcMYBF110 forming a MYB-bHLH-WD40 complex to regulate anthocyanin biosynthesis, instead of it having a direct involvement.

  16. Faba Bean: Transcriptome Analysis from Etiolated Seedling and Developing Seed Coat of Key Cultivars for Synthesis of Proanthocyanidins, Phytate, Raffinose Family Oligosaccharides, Vicine, and Convicine

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    Heather Ray

    2015-03-01

    Full Text Available Faba bean ( L. has been little examined from a genetic or genomic perspective despite its status as an established food and forage crop with some key pharmaceutical factors such as vicine and convicine (VC, which provoke severe haemolysis in genetically susceptible humans. We developed next-generation sequencing libraries to maximize information to elucidate the VC pathway or relevant markers as well as other genes of interest for the species. One selected cultivar, A01155, lacks synthesis of the favism-provoking factors, VC, and is low in tannin, while two cultivars, SSNS-1 and CDC Fatima, are wild-type for these factors. Tissues (5- to 6-d-old root and etiolated shoot and developing seed coat were selected to maximize the utility and breadth of the gene expression profile. Approximately 1.2 × 10 expressed transcripts were sequenced and assembled into contigs. The synthetic pathways for phosphatidylinositol or phytate, the raffinose family oligosaccharides, and proanthocyanidin were examined and found to contain nearly a full complement of the synthetic genes for these pathways. A severe deficiency in anthocyanidin reductase expression was found in the low-tannin cultivar A01155. Approximately 5300 variants, including 234 variants specific to one of the three cultivars, were identified. Differences in expression and variants potentially related to VC synthesis were analyzed using strategies exploiting differences in expression between cultivars and tissues. These sequences should be of high utility for marker-assisted selection for the key traits vicine, convicine, and proanthocyanidin, and should contribute to the scant genetic maps available for this species.

  17. Eugenia jambolana Lam. Berry Extract Inhibits Growth and Induces Apoptosis of Human Breast Cancer but not Non-Tumorigenic Breast Cells

    Science.gov (United States)

    Li, Liya; Adams, Lynn S.; Chen, Shiuan; Killian, Caroline; Ahmed, Aftab; Seeram, Navindra P.

    2009-01-01

    The ripe purple berries of the native Indian plant, Eugenia jambolana Lam., known as Jamun, are popularly consumed and available in the United States in Florida and Hawaii. Despite the growing body of data on the chemopreventive potential of edible berry extracts, there is paucity of such data for Jamun fruit. Therefore our laboratory initiated the current study with the following objectives:1) to prepare a standardized Jamun fruit extract (JFE) for biological studies and, 2) to investigate the anti-proliferative and pro-apoptotic effects of JFE in estrogen dependent/aromatase positive (MCF-7aro), and estrogen independent (MDA-MB-231) breast cancer cells, and in a normal/non-tumorigenic (MCF-10A) breast cell line. JFE was standardized to anthocyanin content using the pH differential method, and individual anthocyanins were identified by high performance liquid chromatography with ultraviolet (HPLC-UV) and tandem mass spectrometry (LC-MS/MS) methods. JFE contained 3.5% anthocyanins (as cyanidin-3-glucoside equivalents) which occur as diglucosides of five anthocyanidins/aglycons: delphinidin, cyanidin, petunidin, peonidin and malvidin. In the proliferation assay, JFE was most effective against MCF-7aro (IC50=27 µg/mL), followed by MDA-MB-231 (IC50=40 µg/mL) breast cancer cells. Importantly, JFE exhibited only mild antiproliferative effects against the normal MCF-10A (IC50>100 µg/mL) breast cells. Similarly, JFE (at 200 µg/mL) exhibited pro-apoptotic effects against the MCF-7aro (p≤0.05) and the MDA-MB-231 (p≤0.01) breast cancer cells, but not towards the normal MCF-10A breast cells. These studies suggest that JFE may have potential beneficial effects against breast cancer. PMID:19166352

  18. A R2R3-MYB transcription factor from Epimedium sagittatum regulates the flavonoid biosynthetic pathway.

    Directory of Open Access Journals (Sweden)

    Wenjun Huang

    Full Text Available Herba epimedii (Epimedium, a traditional Chinese medicine, has been widely used as a kidney tonic and antirheumatic medicine for thousands of years. The bioactive components in herba epimedii are mainly prenylated flavonol glycosides, end-products of the flavonoid pathway. Epimedium species are also used as garden plants due to the colorful flowers and leaves. Many R2R3-MYB transcription factors (TFs have been identified to regulate the flavonoid and anthocyanin biosynthetic pathways. However, little is known about the R2R3-MYB TFs involved in regulation of the flavonoid pathway in Epimedium. Here, we reported the isolation and functional characterization of the first R2R3-MYB TF (EsMYBA1 from Epimedium sagittatum (Sieb. Et Zucc. Maxim. Conserved domains and phylogenetic analysis showed that EsMYBA1 belonged to the subgroup 6 clade (anthocyanin-related MYB clade of R2R3-MYB family, which includes Arabidopsis AtPAP1, apple MdMYB10 and legume MtLAP1. EsMYBA1 was preferentially expressed in leaves, especially in red leaves that contain higher content of anthocyanin. Alternative splicing of EsMYBA1 resulted in three transcripts and two of them encoded a MYB-related protein. Yeast two-hybrid and transient luciferase expression assay showed that EsMYBA1 can interact with several bHLH regulators of the flavonoid pathway and activate the promoters of dihydroflavonol 4-reductase (DFR and anthocyanidin synthase (ANS. In both transgenic tobacco and Arabidopsis, overexpression of EsMYBA1 induced strong anthocyanin accumulation in reproductive and/or vegetative tissues via up-regulation of the main flavonoid-related genes. Furthermore, transient expression of EsMYBA1 in E. sagittatum leaves by Agrobacterium infiltration also induced anthocyanin accumulation in the wounded area. This first functional characterization of R2R3-MYB TFs in Epimedium species will promote further studies of the flavonoid biosynthesis and regulation in medicinal plants.

  19. A R2R3-MYB transcription factor from Epimedium sagittatum regulates the flavonoid biosynthetic pathway.

    Science.gov (United States)

    Huang, Wenjun; Sun, Wei; Lv, Haiyan; Luo, Ming; Zeng, Shaohua; Pattanaik, Sitakanta; Yuan, Ling; Wang, Ying

    2013-01-01

    Herba epimedii (Epimedium), a traditional Chinese medicine, has been widely used as a kidney tonic and antirheumatic medicine for thousands of years. The bioactive components in herba epimedii are mainly prenylated flavonol glycosides, end-products of the flavonoid pathway. Epimedium species are also used as garden plants due to the colorful flowers and leaves. Many R2R3-MYB transcription factors (TFs) have been identified to regulate the flavonoid and anthocyanin biosynthetic pathways. However, little is known about the R2R3-MYB TFs involved in regulation of the flavonoid pathway in Epimedium. Here, we reported the isolation and functional characterization of the first R2R3-MYB TF (EsMYBA1) from Epimedium sagittatum (Sieb. Et Zucc.) Maxim. Conserved domains and phylogenetic analysis showed that EsMYBA1 belonged to the subgroup 6 clade (anthocyanin-related MYB clade) of R2R3-MYB family, which includes Arabidopsis AtPAP1, apple MdMYB10 and legume MtLAP1. EsMYBA1 was preferentially expressed in leaves, especially in red leaves that contain higher content of anthocyanin. Alternative splicing of EsMYBA1 resulted in three transcripts and two of them encoded a MYB-related protein. Yeast two-hybrid and transient luciferase expression assay showed that EsMYBA1 can interact with several bHLH regulators of the flavonoid pathway and activate the promoters of dihydroflavonol 4-reductase (DFR) and anthocyanidin synthase (ANS). In both transgenic tobacco and Arabidopsis, overexpression of EsMYBA1 induced strong anthocyanin accumulation in reproductive and/or vegetative tissues via up-regulation of the main flavonoid-related genes. Furthermore, transient expression of EsMYBA1 in E. sagittatum leaves by Agrobacterium infiltration also induced anthocyanin accumulation in the wounded area. This first functional characterization of R2R3-MYB TFs in Epimedium species will promote further studies of the flavonoid biosynthesis and regulation in medicinal plants.

  20. Heterologous expression of gentian MYB1R transcription factors suppresses anthocyanin pigmentation in tobacco flowers.

    Science.gov (United States)

    Nakatsuka, Takashi; Yamada, Eri; Saito, Misa; Fujita, Kohei; Nishihara, Masahiro

    2013-12-01

    Single-repeat MYB transcription factors, GtMYB1R1 and GtMYB1R9 , were isolated from gentian. Overexpression of these genes reduced anthocyanin accumulation in tobacco flowers, demonstrating their applicability to modification of flower color. RNA interference (RNAi) has recently been used to successfully modify flower color intensity in several plant species. In most floricultural plants, this technique requires prior isolation of target flavonoid biosynthetic genes from the same or closely related species. To overcome this limitation, we developed a simple and efficient method for reducing floral anthocyanin accumulation based on genetic engineering using novel transcription factor genes isolated from Japanese gentians. We identified two single-repeat MYB genes--GtMYB1R and GtMYB1R9--predominantly expressed in gentian petals. Transgenic tobacco plants expressing these genes were produced, and their flowers were analyzed for flavonoid components and expression of flavonoid biosynthetic genes. Transgenic tobacco plants expressing GtMYB1R1 or GtMYB1R9 exhibited significant reductions in floral anthocyanin accumulation, resulting in white-flowered phenotypes. Expression levels of chalcone isomerase (CHI), dihydroflavonol 4-reductase (DFR), and anthocyanidin synthase (ANS) genes were preferentially suppressed in these transgenic tobacco flowers. A yeast two-hybrid assay demonstrated that both GtMYB1R1 and GtMYB1R9 proteins interacted with the GtbHLH1 protein, previously identified as an anthocyanin biosynthesis regulator in gentian flowers. In addition, a transient expression assay indicated that activation of the gentian GtDFR promoter by the GtMYB3-GtbHLH1 complex was partly canceled by addition of GtMYB1R1 or GtMYB1R9. These results suggest that GtMYB1R1 and GtMYB1R9 act as antagonistic transcription factors of anthocyanin biosynthesis in gentian flowers. These genes should consequently be useful for manipulating anthocyanin accumulation via genetic engineering in

  1. Proanthocyanidin accumulation and transcriptional responses in the seed coat of cranberry beans (Phaseolus vulgaris L.) with different susceptibility to postharvest darkening.

    Science.gov (United States)

    Freixas Coutin, José A; Munholland, Seth; Silva, Anjali; Subedi, Sanjeena; Lukens, Lewis; Crosby, William L; Pauls, K Peter; Bozzo, Gale G

    2017-05-25

    Edible dry beans (Phaseolus vulgaris L.) that darken during postharvest storage are graded lower and are less marketable than their non-darkened counterparts. Seed coat darkening in susceptible genotypes is dependent upon the availability of proanthocyanidins, and their subsequent oxidation to reactive quinones. Mature cranberry beans lacking this postharvest darkening trait tend to be proanthocyanidin-deficient, although the underlying molecular and biochemical determinants for this metabolic phenomenon are unknown. Seed coat proanthocyanidin levels increased with plant maturation in a darkening-susceptible cranberry bean recombinant inbred line (RIL), whereas these metabolites were absent in seeds of the non-darkening RIL plants. RNA sequencing (RNA-seq) analysis was used to monitor changes in the seed coat transcriptome as a function of bean development, where transcript levels were measured as fragments per kilobase of exon per million fragments mapped. A total of 1336 genes were differentially expressed between darkening and non-darkening cranberry bean RILs. Structural and regulatory genes of the proanthocyanidin biosynthesis pathway were upregulated in seed coats of the darkening RIL. A principal component analysis determined that changes in transcript levels for two genes of unknown function and three proanthocyanidin biosynthesis genes, FLAVANONE 3-HYDROXYLASE 1, DIHYDROFLAVONOL 4-REDUCTASE 1 and ANTHOCYANIDIN REDUCTASE 1 (PvANR1) were highly correlated with proanthocyanidin accumulation in seed coats of the darkening-susceptible cranberry bean RIL. HPLC-DAD analysis revealed that in vitro activity of a recombinant PvANR1 was NADPH-dependent and assays containing cyanidin yielded epicatechin and catechin; high cyanidin substrate levels inhibited the formation of both of these products. Proanthocyanidin oxidation is a pre-requisite for postharvest-related seed coat darkening in dicotyledonous seeds. In model plant species, the accumulation of

  2. A R2R3-MYB transcription factor regulates the flavonol biosynthetic pathway in a traditional Chinese medicinal plant, Epimedium sagittatum

    Directory of Open Access Journals (Sweden)

    Wenjun Huang

    2016-07-01

    Full Text Available Flavonols as plant secondary metabolites with vital roles in plant development and defense against UV light, have been demonstrated to be the main bioactive components in the genus Epimedium plants, several species of which are used as materials for Herba Epimedii, an important traditional Chinese medicine. The flavonol biosynthetic pathway genes had been already isolated from E. sagittatum, but a R2R3-MYB transcription factor regulating the flavonol synthesis has not been functionally characterized so far in Epimedium plants. In this study, we isolated and characterized the R2R3-MYB transcription factor EsMYBF1 involved in regulation of the flavonol biosynthetic pathway from E. sagittatum. Sequence analysis indicated that EsMYBF1 belongs to the subgroup 7 of R2R3-MYB family which contains the flavonol-specific MYB regulators identified to date. Transient reporter assay showed that EsMYBF1 strongly activated the promoters of EsF3H (flavanone 3-hydroxylase and EsFLS (flavonol synthase, but not the promoters of EsDFRs (dihydroflavonol 4-reductase and EsANS (anthocyanidin synthase in transiently transformed Nicotiana benthamiana leaves. Both yeast two-hybrid assay and transient reporter assay validated EsMYBF1 to be independent of EsTT8, or AtTT8 bHLH regulators of the flavonoid pathway as cofactors. Ectopic expression of EsMYBF1 in transgenic tobacco resulted in the increased flavonol content and the decreased anthocyanin content in flowers. Correspondingly, the structural genes involved in flavonol synthesis were upregulated in the EsMYBF1 overexpression lines, including NtCHS (chalcone synthase, NtCHI (chalcone isomerase, NtF3H and NtFLS, whereas the late biosynthetic genes of the anthocyanin pathway (NtDFR and NtANS were remarkably downregulated, compared to the controls. These results suggest that EsMYBF1 is a flavonol-specific R2R3-MYB regulator, and involved in regulation of the biosynthesis of the flavonol-derived bioactive components in E

  3. Sequence diversity and differential expression of major phenylpropanoid-flavonoid biosynthetic genes among three mango varieties.

    Science.gov (United States)

    Hoang, Van L T; Innes, David J; Shaw, P Nicholas; Monteith, Gregory R; Gidley, Michael J; Dietzgen, Ralf G

    2015-07-30

    Mango fruits contain a broad spectrum of phenolic compounds which impart potential health benefits; their biosynthesis is catalysed by enzymes in the phenylpropanoid-flavonoid (PF) pathway. The aim of this study was to reveal the variability in genes involved in the PF pathway in three different mango varieties Mangifera indica L., a member of the family Anacardiaceae: Kensington Pride (KP), Irwin (IW) and Nam Doc Mai (NDM) and to determine associations with gene expression and mango flavonoid profiles. A close evolutionary relationship between mango genes and those from the woody species poplar of the Salicaceae family (Populus trichocarpa) and grape of the Vitaceae family (Vitis vinifera), was revealed through phylogenetic analysis of PF pathway genes. We discovered 145 SNPs in total within coding sequences with an average frequency of one SNP every 316 bp. Variety IW had the highest SNP frequency (one SNP every 258 bp) while KP and NDM had similar frequencies (one SNP every 369 bp and 360 bp, respectively). The position in the PF pathway appeared to influence the extent of genetic diversity of the encoded enzymes. The entry point enzymes phenylalanine lyase (PAL), cinnamate 4-mono-oxygenase (C4H) and chalcone synthase (CHS) had low levels of SNP diversity in their coding sequences, whereas anthocyanidin reductase (ANR) showed the highest SNP frequency followed by flavonoid 3'-hydroxylase (F3'H). Quantitative PCR revealed characteristic patterns of gene expression that differed between mango peel and flesh, and between varieties. The combination of mango expressed sequence tags and availability of well-established reference PF biosynthetic genes from other plant species allowed the identification of coding sequences of genes that may lead to the formation of important flavonoid compounds in mango fruits and facilitated characterisation of single nucleotide polymorphisms between varieties. We discovered an association between the extent of sequence variation and

  4. RNA-seq Transcriptome Response of Flax (Linum usitatissimum L.) to the Pathogenic Fungus Fusarium oxysporum f. sp. lini.

    Science.gov (United States)

    Galindo-González, Leonardo; Deyholos, Michael K

    2016-01-01

    -related enzymes chalcone synthase, dihydroflavonol reductase and multiple anthocyanidin synthases; and a peroxidase implicated in lignin formation ( PRX52 ). Additionally, regulation of some genes indicated potential pathogen manipulation to facilitate infection; these included four disease resistance proteins that were repressed, indole acetic acid amido/amino hydrolases which were upregulated, activated expansins and glucanases, amino acid transporters and aquaporins, and finally, repression of major latex proteins.

  5. Chemical composition of some Roselle (Hibiscus sabdariffa) genotypes

    International Nuclear Information System (INIS)

    Alshoosh, Wafa Gamal Abdalla

    1997-10-01

    Six lines of of Hibiscus sabdariffa were used in this study. The proximate analysis gave moisture 6.19%, 12.07% and 8.42%, ash 10.6%, 7.98% and 12.42%, protein 9.76%, 5.53% and 6.13%, oil 0.99%, 0.95% and 0.90%, fibre 10.74%, 11.73% and 12.17%, carbohydrate 61.64%, 61.76% and 60.43% for seasons 93/94, 94/95 and 95/96 respectively. Physicochemical investigation of karkade calices gave the following results: reducing sugar 1.29%. 1.28% and 1.27%, non reducing sugar 0.87, 0.77 and 0.86, PH 3.1, 2.71 and 3.001, colour intensity 0.77, 0.72 and 0.51, insoluble solids 37.74%, 36.36% and 37.33% for seasons 93/94, 94/95 and 95/96 respectively. The value of vitamin C and acidity (organic acids) in season 93/94 was 92.06 mg/100g and 19.58% respectively. Organic acids as hibiscic acid, citric acid, vitamin C and xalic acid was 25.51%, 14.15%, 92.69 mg/100g and 0.55% and 26.18%, 14.14%, 97.26 mg/100g and 0.56% for season 94/95 and 95/96 respectively. Mineral contents for karkade calices were measured by using atomic absorption spectroscopy, the results for season 94/95 were 0.56%, 0.24%, 0.08%, 0.23%, 0.95% and 0.19% for Ca, Mg, Fe, Na, K and P respectively, while mineral content for season 95/96, 1.9%, 0.31%, 0.07%, 0.31%, 0.48%, 0.23%. 0.05%, 0.22%, 0.06%, 0.006%, 0.02%, and 0.03% for Ca, Mg, Fe, Na, K, P, Zn, M, Cu, Pb, Co and Cr respectively. UV-visible spectrum showed the presence of the following pigments: dephinidin-3-sambubioside and cyanidin-3-sambuioside. Total anthocyanin of karkade calices were found to be 0.89 to 1.4% and 0.99 to 1.6% for season 94/95 and 95/96 respectively. Acid hydrolysis of the pigments showed the presence of xylose and glucose in addition to the anthocyanidins delphinidin ad cyanidin.(Author)

  6. MYB and bHLH transcription factor transgenes increase anthocyanin pigmentation in petunia and lisianthus plants, and the petunia phenotypes are strongly enhanced under field conditions

    Directory of Open Access Journals (Sweden)

    Kathy E Schwinn

    2014-11-01

    Full Text Available Petunia line Mitchell [MP, Petunia axillaris × (P. axillaris × P. hybrida] and Eustoma grandiflorum (lisianthus plants were produced containing a transgene for over-expression of the R2R3-MYB transcription factor (ROSEA1 that up-regulates flavonoid biosynthesis in Antirrhinum majus. The petunia lines were also crossed with previously produced MP lines containing a Zea mays flavonoid-related bHLH transcription factor transgene (LEAF COLOR, LC, which induces strong vegetative pigmentation when these 35S:LC plants are exposed to high light levels. 35S:ROS1 lisianthus transgenics had limited changes in anthocyanin pigmentation, specifically, precocious pigmentation of flower petals and increased pigmentation of sepals. RNA transcript levels for two anthocyanin biosynthetic genes, chalcone synthase and anthocyanidin synthase, were increased in the 35S:ROS1 lisianthus petals compared to those of control lines. With MP, the 35S:ROS1 calli showed novel red pigmentation in culture, but this was generally not seen in tissue culture plantlets regenerated from the calli or young plants transferred to soil in the greenhouse. Anthocyanin pigmentation was enhanced in the stems of mature 35S:ROS1 MP plants, but the MP white-flower phenotype was not complemented. Progeny from a 35S:ROS1×35S:LC cross had novel pigmentation phenotypes that were not present in either parental line or MP. In particular, there was increased pigment accumulation in the petal throat region, and the anthers changed from yellow to purple colour. An outdoor field trial was conducted with the 35S:ROS1, 35S:LC, 35S:ROS1×35S:LC and control MP lines. Field conditions rapidly induced intense foliage pigmentation in 35S:LC plants, a phenotype not observed in control MP or equivalent 35S:LC plants maintained in a greenhouse. No difference in plant stature, seed germination, or plant survival was observed between transgenic and control plants.

  7. Anti-inflammatory and antioxidant activities of the Impatiens noli-tangere and Stachys officinalis polyphenolic-rich extracts

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    Gabriela Paun

    Full Text Available ABSTRACT This study evaluated the anti-inflammatory and antioxidant activities of Impatiens noli-tangere L., Balsaminaceae, and of Stachys officinalis L., Lamiaceae, polyphenolic-rich extracts obtained by nanofiltration process. Results showed the great potential and efficiency of the nanofiltration process to concentrate the herbal extract's main polyphenolic compounds (over 91% phenolic acids and flavonoids retention. S. officinalis polyphenolic-rich extracts had high antioxidant activities (IC50 2.5 µg/ml compared to I. noli-tangere polyphenolic-rich extracts (IC50 19.3 µg/ml and similar with that of ascorbic acid. Polyphenolic-rich extracts were investigated to determine the pro-inflammatory enzymes lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2 and their inhibitory activity. Furthermore, high inhibitory activity of the examined extracts was reported for the first time, for both lipoxygenase (IC50 2.46 and 1.22 µg/ml for I. noli-tangere and S. officinalis polyphenolic-rich extracts, respectively, cyclooxygenase-1 (IC50 18.4 and 10.1 µg/ml for I. noli-tangere and S. officinalis polyphenolic-rich extracts, respectively and cyclooxygenase-2 (IC50 = 1.9 and 1.2 mg/ml for I. noli-tangere and S. officinalis polyphenolic-rich extracts, respectively. Additionally, the in vivo studies showed that S. officinalis polyphenolic-rich extract has a higher anti-inflammatory effect, the hind-paw volume employed for both models determined that I. noli-tangere polyphenolic-rich extract and is also higher than that of diclofenac. It was noticed that their anti-inflammatory effect persists for more than 24 h. The I. noli-tangere and S. officinalis polyphenolic-rich extracts exert anti-inflammatory and antioxidant activities and these properties can be at least partly assigned to the presence of ursolic acid, caffeic acid, rosmarinic acid, quercetin and also anthocyanidins (genistin. The obtained results indicate the anti-inflammatory potential of the

  8. Chemical composition of some Roselle (Hibiscus sabdariffa) genotypes

    Energy Technology Data Exchange (ETDEWEB)

    Alshoosh, Wafa Gamal Abdalla [Department of food science and technology, Faculty of Agriculture, University of Khartoum, Khartoum (Sudan)

    1997-10-01

    Six lines of of Hibiscus sabdariffa were used in this study. The proximate analysis gave moisture 6.19%, 12.07% and 8.42%, ash 10.6%, 7.98% and 12.42%, protein 9.76%, 5.53% and 6.13%, oil 0.99%, 0.95% and 0.90%, fibre 10.74%, 11.73% and 12.17%, carbohydrate 61.64%, 61.76% and 60.43% for seasons 93/94, 94/95 and 95/96 respectively. Physicochemical investigation of karkade calices gave the following results: reducing sugar 1.29%. 1.28% and 1.27%, non reducing sugar 0.87, 0.77 and 0.86, PH 3.1, 2.71 and 3.001, colour intensity 0.77, 0.72 and 0.51, insoluble solids 37.74%, 36.36% and 37.33% for seasons 93/94, 94/95 and 95/96 respectively. The value of vitamin C and acidity (organic acids) in season 93/94 was 92.06 mg/100g and 19.58% respectively. Organic acids as hibiscic acid, citric acid, vitamin C and xalic acid was 25.51%, 14.15%, 92.69 mg/100g and 0.55% and 26.18%, 14.14%, 97.26 mg/100g and 0.56% for season 94/95 and 95/96 respectively. Mineral contents for karkade calices were measured by using atomic absorption spectroscopy, the results for season 94/95 were 0.56%, 0.24%, 0.08%, 0.23%, 0.95% and 0.19% for Ca, Mg, Fe, Na, K and P respectively, while mineral content for season 95/96, 1.9%, 0.31%, 0.07%, 0.31%, 0.48%, 0.23%. 0.05%, 0.22%, 0.06%, 0.006%, 0.02%, and 0.03% for Ca, Mg, Fe, Na, K, P, Zn, M, Cu, Pb, Co and Cr respectively. UV-visible spectrum showed the presence of the following pigments: dephinidin-3-sambubioside and cyanidin-3-sambuioside. Total anthocyanin of karkade calices were found to be 0.89 to 1.4% and 0.99 to 1.6% for season 94/95 and 95/96 respectively. Acid hydrolysis of the pigments showed the presence of xylose and glucose in addition to the anthocyanidins delphinidin ad cyanidin.(Author) 90 refs. , 18 tabs. , 14 figs.

  9. Differential expression of anthocyanin biosynthetic genes in relation to anthocyanin accumulation in the pericarp of Litchi chinensis Sonn.

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    Yong-Zan Wei

    Full Text Available Litchi has diverse fruit color phenotypes, yet no research reflects the biochemical background of this diversity. In this study, we evaluated 12 litchi cultivars for chromatic parameters and pigments, and investigated the effects of abscisic acid, forchlorofenron (CPPU, bagging and debagging treatments on fruit coloration in cv. Feizixiao, an unevenly red cultivar. Six genes encoding chalcone synthase (CHS, chalcone isomerase (CHI, flavanone 3-hydroxylase (F3H, dihydroflavonol 4-reductase (DFR, anthocyanidin synthase (ANS and UDP-glucose: flavonoid 3-O-glucosyltransferase (UFGT were isolated from the pericarp of the fully red litchi cv. Nuomici, and their expression was analyzed in different cultivars and under the above mentioned treatments. Pericarp anthocyanin concentration varied from none to 734 mg m(-2 among the 12 litchi cultivars, which were divided into three coloration types, i.e. non-red ('Kuixingqingpitian', 'Xingqiumili', 'Yamulong'and 'Yongxing No. 2', unevenly red ('Feizixiao' and 'Sanyuehong' and fully red ('Meiguili', 'Baila', Baitangying' 'Guiwei', 'Nuomici' and 'Guinuo'. The fully red type cultivars had different levels of anthocyanin but with the same composition. The expression of the six genes, especially LcF3H, LcDFR, LcANS and LcUFGT, in the pericarp of non-red cultivars was much weaker as compared to those red cultivars. Their expression, LcDFR and LcUFGT in particular, was positively correlated with anthocyanin concentrations in the pericarp. These results suggest the late genes in the anthocyanin biosynthetic pathway were coordinately expressed during red coloration of litchi fruits. Low expression of these genes resulted in absence or extremely low anthocyanin accumulation in non-red cultivars. Zero-red pericarp from either immature or CPPU treated fruits appeared to be lacking in anthocyanins due to the absence of UFGT expression. Among these six genes, only the expression of UFGT was found significantly correlated

  10. RNA-seq Transcriptome Response of Flax (Linum usitatissimum L. to the Pathogenic Fungus Fusarium oxysporum f. sp. lini.

    Directory of Open Access Journals (Sweden)

    Leonardo Miguel Galindo-González

    2016-11-01

    -related enzymes chalcone synthase, dihydroflavonol reductase and multiple anthocyanidin synthases; and a peroxidase implicated in lignin formation (PRX52. Additionally, regulation of some genes indicated potential pathogen manipulation to facilitate infection; these included four disease resistance proteins that were repressed, indole acetic acid amido/amino hydrolases which were upregulated, activated expansins and glucanases, amino acid transporters and aquaporins, and finally, repression of major latex proteins.

  11. Medicinal flora of the Cholistan desert: a review

    International Nuclear Information System (INIS)

    Hmeed, M.; Ashraf, M.; Nawaz, T.; Naz, N.; Ahmad, M.S.A.; Al-Quriany, F.; Younis, A.

    2011-01-01

    The Cholistan desert can be divided into two distinct regions on the basis of topography, soil type and texture, and vegetation structure: the northern Lesser Cholistan and southern Greater Cholistan. The desert is characterized by large saline compacted areas with alluvial clay, sandy ridges and dunes, and semi-stabilized to frequently shifting dunes. The climate is subtropical, harsh, hot and arid, and influenced by seasonal monsoons. Vegetation cover on the sand dunes is comprised by a few tussock-forming grasses including Cenchrus ciliaris, Panicum turgidum and Lasiurus scindicus, along with perennial shrubs Calligonum polygonoides, Leptadenia pyrotechnica and Aerva javanica. Interdunal flats are dominated by grasses, mainly Cymbopogon jwarancusa, Sporobolus ioclados, Panicum antidotale, and Ochthochloa compressa, and tall shrubs Calligonum polygonoides and Capparis decidua. Vegetation of saline patches is specific, dominated by halophytes mainly belonging to family Chenopodiaceae (Amaranthaceae). Many plants of the Cholistan desert, including Neurada procumbens, Aerva javanica, Capparis decidua, Cleome brachycarpa, Dipterygium glaucum, Gisekia pharnacioides, Suaeda fruticosa, Achyranthes aspera, Aerva javanica, Alhagi maurorum, Calotropis procera, Capparis decidua, Zaleya pentandra, Mollugo cerviana, Ziziphus mauritiana, Boerhavia procumbens, Cressa cretica and Crotalaria burhia, are frequently used by the local inhabitants to cure chronic and acute diseases. A variety of medicinally important chemical compounds have been extracted and identified from the plants of the Cholistan desert, including terpenes and triterpenoids, sterols and steroids, phenolics, flavonoids, gums and resins, quinones, anthocyanidines, saponins, antioxidants and fatty acids. Habitat degradation, intensive agricultural practices and over exploitation of resources pose a serious threat to the diversity of ethno botanically important plant species. Allopathic medicines are generally

  12. Constraint-Based Modeling Highlights Cell Energy, Redox Status and α-Ketoglutarate Availability as Metabolic Drivers for Anthocyanin Accumulation in Grape Cells Under Nitrogen Limitation

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    Eric Soubeyrand

    2018-05-01

    Full Text Available Anthocyanin biosynthesis is regulated by environmental factors (such as light, temperature, and water availability and nutrient status (such as carbon, nitrogen, and phosphate nutrition. Previous reports show that low nitrogen availability strongly enhances anthocyanin accumulation in non carbon-limited plant organs or cell suspensions. It has been hypothesized that high carbon-to-nitrogen ratio would lead to an energy excess in plant cells, and that an increase in flavonoid pathway metabolic fluxes would act as an “energy escape valve,” helping plant cells to cope with energy and carbon excess. However, this hypothesis has never been tested directly. To this end, we used the grapevine Vitis vinifera L. cultivar Gamay Teinturier (syn. Gamay Freaux or Freaux Tintorier, VIVC #4382 cell suspension line as a model system to study the regulation of anthocyanin accumulation in response to nitrogen supply. The cells were sub-cultured in the presence of either control (25 mM or low (5 mM nitrate concentration. Targeted metabolomics and enzyme activity determinations were used to parametrize a constraint-based model describing both the central carbon and nitrogen metabolisms and the flavonoid (phenylpropanoid pathway connected by the energy (ATP and reducing power equivalents (NADPH and NADH cofactors. The flux analysis (2 flux maps generated, for control and low nitrogen in culture medium clearly showed that in low nitrogen-fed cells all the metabolic fluxes of central metabolism were decreased, whereas fluxes that consume energy and reducing power, were either increased (upper part of glycolysis, shikimate, and flavonoid pathway or maintained (pentose phosphate pathway. Also, fluxes of flavanone 3β-hydroxylase, flavonol synthase, and anthocyanidin synthase were strongly increased, advocating for a regulation of the flavonoid pathway by alpha-ketoglutarate levels. These results strongly support the hypothesis of anthocyanin biosynthesis acting as

  13. MYB and bHLH transcription factor transgenes increase anthocyanin pigmentation in petunia and lisianthus plants, and the petunia phenotypes are strongly enhanced under field conditions

    Science.gov (United States)

    Schwinn, Kathy E.; Boase, Murray R.; Bradley, J. Marie; Lewis, David H.; Deroles, Simon C.; Martin, Cathie R.; Davies, Kevin M.

    2014-01-01

    Petunia line Mitchell [MP, Petunia axillaris × (P. axillaris × P. hybrida)] and Eustoma grandiflorum (lisianthus) plants were produced containing a transgene for over-expression of the R2R3-MYB transcription factor [TF; ROSEA1 (ROS1)] that up-regulates flavonoid biosynthesis in Antirrhinum majus. The petunia lines were also crossed with previously produced MP lines containing a Zea mays flavonoid-related basic helix-loop-helix TF transgene (LEAF COLOR, LC), which induces strong vegetative pigmentation when these 35S:LC plants are exposed to high-light levels. 35S:ROS1 lisianthus transgenics had limited changes in anthocyanin pigmentation, specifically, precocious pigmentation of flower petals and increased pigmentation of sepals. RNA transcript levels for two anthocyanin biosynthetic genes, chalcone synthase and anthocyanidin synthase, were increased in the 35S:ROS1 lisianthus petals compared to those of control lines. With MP, the 35S:ROS1 calli showed novel red pigmentation in culture, but this was generally not seen in tissue culture plantlets regenerated from the calli or young plants transferred to soil in the greenhouse. Anthocyanin pigmentation was enhanced in the stems of mature 35S:ROS1 MP plants, but the MP white-flower phenotype was not complemented. Progeny from a 35S:ROS1 × 35S:LC cross had novel pigmentation phenotypes that were not present in either parental line or MP. In particular, there was increased pigment in the petal throat region, and the anthers changed from yellow to purple pigmentation. An outdoor field trial was conducted with the 35S:ROS1, 35S:LC, 35S:ROS1 × 35S:LC and control MP lines. Field conditions rapidly induced intense foliage pigmentation in 35S:LC plants, a phenotype not observed in control MP or equivalent 35S:LC plants maintained in a greenhouse. No difference in plant stature, seed germination, or plant survival was observed between transgenic and control plants. PMID:25414715

  14. Characterization of anthocyanins in the hybrid progenies derived from Iris dichotoma and I. domestica by HPLC-DAD-ESI/MS analysis.

    Science.gov (United States)

    Xu, Wenji; Luo, Gangjun; Yu, Fengyang; Jia, Qingxiang; Zheng, Yang; Bi, Xiaoying; Lei, Jiajun

    2018-06-01

    contained three to six anthocyanins. Petals of the orange, red, and pink groups contained two to four major anthocyanins. The total variance explained by the first two principal components (PC) in a PC analysis of the intensities of the compound peaks detected in individuals representing the eight color groups was 44.7%. Individuals were classified into 10 types (A-I to A-X) according to their anthocyanidin composition in the flower petals. Knowledge of the types of anthocyanins determining flower petal color will aid comprehensive understanding of flower color characteristics in hybrid progeny and will contribute to the development of breeding Iris cultivars of diverse flower colors. Copyright © 2018 Elsevier Ltd. All rights reserved.

  15. Quantitative changes in proteins responsible for flavonoid and anthocyanin biosynthesis in strawberry fruit at different ripening stages: A targeted quantitative proteomic investigation employing multiple reaction monitoring.

    Science.gov (United States)

    Song, Jun; Du, Lina; Li, Li; Kalt, Wilhelmina; Palmer, Leslie Campbell; Fillmore, Sherry; Zhang, Ying; Zhang, ZhaoQi; Li, XiHong

    2015-06-03

    To better understand the regulation of flavonoid and anthocyanin biosynthesis, a targeted quantitative proteomic investigation employing LC-MS with multiple reaction monitoring was conducted on two strawberry cultivars at three ripening stages. This quantitative proteomic workflow was improved through an OFFGEL electrophoresis to fractionate peptides from total protein digests. A total of 154 peptide transitions from 47 peptides covering 21 proteins and isoforms related to anthocyanin biosynthesis were investigated. The normalized protein abundance, which was measured using isotopically-labeled standards, was significantly changed concurrently with increased anthocyanin content and advanced fruit maturity. The protein abundance of phenylalanine ammonia-lyase; anthocyanidin synthase, chalcone isomerase; flavanone 3-hydroxylase; dihydroflavonol 4-reductase, UDP-glucose:flavonoid-3-O-glucosyltransferase, cytochrome c and cytochrome C oxidase subunit 2, was all significantly increased in fruit of more advanced ripeness. An interaction between cultivar and maturity was also shown with respect to chalcone isomerase. The good correlation between protein abundance and anthocyanin content suggested that a metabolic control point may exist for anthocyanin biosynthesis. This research provides insights into the process of anthocyanin formation in strawberry fruit at the level of protein concentration and reveals possible candidates in the regulation of anthocyanin formation during fruit ripening. To gain insight into the molecular mechanisms contributing to flavonoids and anthocyanin biosynthesis and regulation of strawberry fruit during ripening is challenging due to limited molecular biology tools and established hypothesis. Our targeted proteomic approach employing LC-MS/MS analysis and MRM technique to quantify proteins in relation to flavonoids and anthocyanin biosynthesis and regulation in strawberry fruit during fruit ripening is novel. The identification of peptides

  16. Effects of Organic and Chemical Fertilizers on some Quantitative Traits and Anthocyanin of Roselle under Zabol conditions

    Directory of Open Access Journals (Sweden)

    rahman Ebrahimzadeh abdashti

    2017-02-01

    increased the height, number of branches and stem diameter per plant in different stages of growth. Mean comparison showed that there were significant differences between the treatments and control in most traits, so that the maximum height, number of branches and stem diameter belonged to the treatment of organic and chemical fertilizer with humic acid (T8, T9 and T10. The highest number of fruits and seed yield per plant (41/98% was obtained from the T9 treatment compared to the control. This result was corresponded with the results of other researchers in the roselle. The result showed that inflorescence length, length and diameter of fruit had the highest values by using the cattle manure + humic acid (T8; and so measured characters had the lowest values in control treatment. Effect of different fertilizer treatments on fruit fresh weight, fresh and dry weights of sepals had statistically significant differences. The highest and the lowest values of fruit fresh weight, fresh and dry weights of sepals were obtained from T9 treatment (compost + humic acid and control treatment, respectively. Compost improves conditions for the plant growth. Humic acid stimulates the growth hormone and increases the absorption of nutrients by plant. So, with these reasons it seems that higher growth features and further calyx yield were achieved by applying compost + humic acid than other treatments. The effect of treatments organic and chemical fertilizers with humic acid on the amount of anthocyanin was higher compared with using them separately. Compost, vermicompost and cattle manure fertilizers are containing humic acid substances and humic acid (phenolic compound derivatives is a precursor for the synthesis of anthocyanidin (flavonoid structure, therefore they correlated with the increasing anthocyanin in treatments organic fertilizers and chemical with humic acid. Conclusions: The results showed that all applied fertilizers treatments improved growth features, further calyx yield

  17. A genomics investigation of partitioning into and among flavonoid-derived condensed tannins for carbon sequestration in Populus

    Energy Technology Data Exchange (ETDEWEB)

    Harding, Scott, A; Tsai, Chung-jui; Lindroth, Richard, L

    2013-03-24

    constituted a metabolic carbon drain in developing leaves that was not observed in the roots. We propose that PEA, in addition to other factors, including flavonoid pathway Myb transcription factors, is an important contributor to carbon management and plant defense in Populus. Objective 3: From work related to the first two objectives, it appeared that CT chemistry, at least in terms of the proportions of mono, di and tri hydroxylation at the phenylpropanoid-derived B-ring, changed little if at all when CT accrual per unit time was increased. A large number of transgenic Populus plants with alterations in the expression of flavonoid pathway genes and the potential to produce B-ring, chemically altered CT were generated during the project. Transgenic lines of Populus tremula Michx. Populus alba L. clone 717-1B4, a low CT producer, were produced that over- or under-express several mid and late flavonoid pathway genes including dihydroxyflavonol reductase (DFR-2 isoforms), leucoanthocyanidin reductase (LAR-3 isoforms), anthocyanidin reductase (ANR-2 isoforms), flavonol synthase (FLS-2 isoforms). A large number of additional transformation constructs (chalcone synthases, flavone synthases, and flavanol hydroxylases) were developed that failed to result in transgenic plants. We have purified CT from several of the successful lines and have obtained evidence from pyrolysis GC-MS that CT chemical composition was altered in transgenic lines harboring overexpression constructs for one of the two DFR isoforms. We have also observed increased CT levels in leaves of those lines, but the increases vary substantially in magnitude from experiment to experiment which has led to ongoing efforts to understand the variation before attempting to publish the findings. Preliminary results from some of the transgenic work were presented: An C*, Luo K, El Kayal W, Harding SA, Tsai C-J (2009) Transgenic manipulation of condensed tannins in Populus. IUFRO Tree Biotechnology Conference, Whistler, BC