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Journal articles on the topic 'Pyranoanthocyanin'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Miyagusuku-Cruzado, Gonzalo, Danielle M. Voss, and M. Monica Giusti. "Influence of the Anthocyanin and Cofactor Structure on the Formation Efficiency of Naturally Derived Pyranoanthocyanins." International Journal of Molecular Sciences 22, no. 13 (June 23, 2021): 6708. http://dx.doi.org/10.3390/ijms22136708.

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Pyranoanthocyanins are anthocyanin-derived pigments with higher stability to pH and storage. However, their slow formation and scarcity in nature hinder their industrial application. Pyranoanthocyanin formation can be accelerated by selecting anthocyanin substitutions, cofactor concentrations, and temperature. Limited information is available on the impacts of the chemical structure of the cofactor and anthocyanin; therefore, we evaluated their impacts on pyranoanthocyanin formation efficiency under conditions reported as favorable for the reaction. Different cofactors were evaluated including pyruvic acid, acetone, and hydroxycinnamic acids (p-coumaric, caffeic, ferulic, and sinapic acid) by incubating them with anthocyanins in a molar ratio of 1:30 (anthocyanin:cofactor), pH 3.1, and 45 °C. The impact of the anthocyanin aglycone was evaluated by incubating delphinidin, cyanidin, petunidin, or malvidin derivatives with the most efficient cofactor (caffeic acid) under identical conditions. Pigments were identified using UHPLC-PDA and tandem mass spectrometry, and pyranoanthocyanin formation was monitored for up to 72 h. Pyranoanthocyanin yields were the highest with caffeic acid (~17% at 72 h, p < 0.05). When comparing anthocyanins, malvidin-3-O-glycosides yielded twice as many pyranoanthocyanins after 24 h (~20%, p < 0.01) as cyanidin-3-O-glycosides. Petunidin- and delphinidin-3-O-glycosides yielded <2% pyranoanthocyanins. This study demonstrated the importance of anthocyanin and cofactor selection in pyranoanthocyanin production.

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2

Marquez, Ana, María P. Serratosa, and Julieta Merida. "Pyranoanthocyanin Derived Pigments in Wine: Structure and Formation during Winemaking." Journal of Chemistry 2013 (2013): 1–15. http://dx.doi.org/10.1155/2013/713028.

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In recent years many studies have been carried out on new pigments derived from anthocyanins that appear in wine during processing and aging. This paper aims to summarize the latest research on these compounds, focusing on the structure and the formation process. The main pyranoanthocyanins are formed from the reaction between the anthocyanins and some metabolites released during the yeast fermentation: carboxypyranoanthocyanins or type A vitisins, formed upon the reaction between the enol form of the pyruvic acid and the anthocyanins; type B vitisins, formed by the cycloaddition of an acetaldehyde molecule on an anthocyanin; methylpyranoanthocyanins, resulted from the reaction between acetone and anthocyanins; pinotins resulted from the covalent reaction between the hydroxycinnamic acids and anthocyanins; and finally flavanyl-pyranoanthocyanins. On the other hand, the second generation of compounds has also been reviewed, where the initial compound is a pyranoanthocyanin. This family includes oxovitisins, vinylpyranoanthocyanins, pyranoanthocyanins linked through a butadienylidene bridge, and pyranoanthocyanin dimers.

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3

Mateus, N., J. Oliveira, A. M. González-Paramás, C. Santos-Buelga, and V. de Freitas. "Screening of Portisins (Vinylpyranoanthocyanin Pigments) in Port Wine by LC/DAD-MS." Food Science and Technology International 11, no. 5 (October 2005): 353–58. http://dx.doi.org/10.1177/1082013205057940.

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Samples of a two-year-old Port red wine were fractionated by Toyopearl gel column chromatography yielding different coloured fractions. Anthocyanin-derived compounds were tentatively identified by LC/DAD-MS in the different eluted fractions. Several pigments were found to correspond to a recently reported family of pyranoanthocyanin compounds named portisins, supposedly arising from the reaction between anthocyanin-pyruvic acid adducts and flavanols in the presence of acetaldehyde. These pigments present a structure in which pyranoanthocyanins are linked to flavanols (catechins or procyanidin dimers) through a vinyl linkage. These pigments showed a UV-visible spectrum with a λmax batochromically shifted from that of genuine anthocyanins, thereby contributing to a more bluish hue.

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4

Zhu, Zhenzhou, Nao Wu, Minjie Kuang, Olusola Lamikanra, Gang Liu, Shuyi Li, and Jingren He. "Preparation and toxicological evaluation of methyl pyranoanthocyanin." Food and Chemical Toxicology 83 (September 2015): 125–32. http://dx.doi.org/10.1016/j.fct.2015.05.004.

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5

Siddique, Farhan, Cassio P. Silva, Gustavo T. Medeiros Silva, Hans Lischka, Frank H. Quina, and Adelia J. A. Aquino. "The electronic transitions of analogs of red wine pyranoanthocyanin pigments." Photochemical & Photobiological Sciences 18, no. 1 (2019): 45–53. http://dx.doi.org/10.1039/c8pp00391b.

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6

da Silva, Cassio Pacheco, Renan Moraes Pioli, Liu Liu, Shasha Zheng, Mengjiao Zhang, Gustavo Thalmer de Medeiros Silva, Vânia Maria Teixeira Carneiro, and Frank H. Quina. "Improved Synthesis of Analogues of Red Wine Pyranoanthocyanin Pigments." ACS Omega 3, no. 1 (January 25, 2018): 954–60. http://dx.doi.org/10.1021/acsomega.7b01955.

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7

Lu, Yinrong, and L. Yeap Foo. "Unusual anthocyanin reaction with acetone leading to pyranoanthocyanin formation." Tetrahedron Letters 42, no. 7 (February 2001): 1371–73. http://dx.doi.org/10.1016/s0040-4039(00)02246-2.

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8

Pinto, Ana Lucia, Hugo Cruz, Joana Oliveira, Paula Araújo, Luis Cruz, Vânia Gomes, Cassio P. Silva, et al. "Dye-sensitized solar cells based on dimethylamino-π-bridge-pyranoanthocyanin dyes." Solar Energy 206 (August 2020): 188–99. http://dx.doi.org/10.1016/j.solener.2020.05.101.

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9

Araújo, Paula, Ana Costa, Iva Fernandes, Nuno Mateus, Victor de Freitas, Bruno Sarmento, and Joana Oliveira. "Stabilization of bluish pyranoanthocyanin pigments in aqueous systems using lignin nanoparticles." Dyes and Pigments 166 (July 2019): 367–74. http://dx.doi.org/10.1016/j.dyepig.2019.03.020.

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10

Oliveira, Joana, Nuno Mateus, José E. Rodriguez-borges, Eurico J. Cabrita, Artur M. S. Silva, and Victor de Freitas. "Synthesis of a new pyranoanthocyanin dimer linked through a methyl-methine bridge." Tetrahedron Letters 52, no. 23 (June 2011): 2957–60. http://dx.doi.org/10.1016/j.tetlet.2011.03.125.

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11

He, Jingren, Alexandre R. F. Carvalho, Nuno Mateus, and Victor De Freitas. "Spectral Features and Stability of Oligomeric Pyranoanthocyanin-flavanol Pigments Isolated from Red Wines." Journal of Agricultural and Food Chemistry 58, no. 16 (August 25, 2010): 9249–58. http://dx.doi.org/10.1021/jf102085e.

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12

Silva, Gustavo Thalmer M., Karen M. da Silva, Cassio P. Silva, Ana Clara B. Rodrigues, Jessy Oake, Marcelo H. Gehlen, Cornelia Bohne, and Frank H. Quina. "Highly fluorescent hybrid pigments from anthocyanin- and red wine pyranoanthocyanin-analogs adsorbed on sepiolite clay." Photochemical & Photobiological Sciences 18, no. 7 (2019): 1750–60. http://dx.doi.org/10.1039/c9pp00141g.

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13

Oliveira, Joana, Joana Azevedo, Artur M. S. Silva, Natércia Teixeira, Luis Cruz, Nuno Mateus, and Victor de Freitas. "Pyranoanthocyanin Dimers: A New Family of Turquoise Blue Anthocyanin-Derived Pigments Found in Port Wine." Journal of Agricultural and Food Chemistry 58, no. 8 (April 28, 2010): 5154–59. http://dx.doi.org/10.1021/jf9044414.

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14

Zhu, Xiaoyi, and M. Monica Giusti. "Pyranoanthocyanin formation rates and yields as affected by cyanidin-3-substitutions and pyruvic or caffeic acids." Food Chemistry 345 (May 2021): 128776. http://dx.doi.org/10.1016/j.foodchem.2020.128776.

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15

Topić Božič, Jelena, Natka Ćurko, Karin Kovačević Ganić, Lorena Butinar, Alen Albreht, Irena Vovk, Dorota Korte, and Branka Mozetič Vodopivec. "Synthesis of pyranoanthocyanins from Pinot Noir grape skin extract using fermentation with high pyranoanthocyanin producing yeasts and model wine storage as potential approaches in the production of stable natural food colorants." European Food Research and Technology 246, no. 6 (April 3, 2020): 1141–52. http://dx.doi.org/10.1007/s00217-020-03467-2.

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16

Vallverdú-Queralt, Anna, Emmanuelle Meudec, Nayla Ferreira-Lima, Nicolas Sommerer, Olivier Dangles, Véronique Cheynier, and Christine Le Guernevé. "A comprehensive investigation of guaiacyl-pyranoanthocyanin synthesis by one-/two-dimensional NMR and UPLC–DAD–ESI–MSn." Food Chemistry 199 (May 2016): 902–10. http://dx.doi.org/10.1016/j.foodchem.2015.12.089.

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17

He, Jingren, Celestino Santos-Buelga, Nuno Mateus, and Victor de Freitas. "Isolation and quantification of oligomeric pyranoanthocyanin-flavanol pigments from red wines by combination of column chromatographic techniques." Journal of Chromatography A 1134, no. 1-2 (November 2006): 215–25. http://dx.doi.org/10.1016/j.chroma.2006.09.011.

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18

Escott, Carlos, Antonio Morata, Jorge Ricardo-da-Silva, María Callejo, María González, and José Suarez-Lepe. "Effect of Lachancea thermotolerans on the Formation of Polymeric Pigments during Sequential Fermentation with Schizosaccharosmyces pombe and Saccharomyces cerevisiae." Molecules 23, no. 9 (September 14, 2018): 2353. http://dx.doi.org/10.3390/molecules23092353.

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Anthocyanins in red grape musts may evolve during the winemaking process and wine aging for several different reasons; colour stability and evolution is a complex process that may depend on grape variety, winemaking technology, fermentative yeast selection, co-pigmentation phenomena and polymerization. The condensation of flavanols with anthocyanins may occur either with the flavylium ion or with the hemiacetal formation in order to produce oligomers and polymers. The kinetics of the reaction are enhanced by the presence of metabolic acetaldehyde, promoting the formation of pyranoanthocyanin-type dimers or flavanol-ethyl-anthocyanin structures. The experimental design carried out using white must corrected with the addition of malvidin-3-O-glucoside and flavanols, suggests that non-Saccharomyces yeasts are able to provide increased levels of colour intensity and larger polymeric pigment ratios and polymerization indexes. The selection of non-Saccharomyces genera, in particular Lachancea thermotolerans and Schizosaccharomyces pombe in sequential fermentation, have provided experimental wines with increased fruity esters, as well as producing wines with potential pigment compositions, even though there is an important reduction of total anthocyanins.

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19

Oliveira, Joana, Ana Fernandes, and Victor de Freitas. "Synthesis and structural characterization by LC–MS and NMR of a new semi-natural blue amino-based pyranoanthocyanin compound." Tetrahedron Letters 57, no. 11 (March 2016): 1277–81. http://dx.doi.org/10.1016/j.tetlet.2016.02.026.

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20

Straathof, Nicole, and M. Monica Giusti. "Improvement of Naturally Derived Food Colorant Performance with Efficient Pyranoanthocyanin Formation from Sambucus nigra Anthocyanins Using Caffeic Acid and Heat." Molecules 25, no. 24 (December 18, 2020): 5998. http://dx.doi.org/10.3390/molecules25245998.

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Consumers and regulations encourage the use of naturally derived food colorants. Anthocyanins (ACN), plant pigments, are unstable in foods. In aged red wines, ACN with a free hydroxyl group at C-5 condenses to form pyranoanthocyanins (PACN), which are more stable but form inefficiently. This study attempted to produce PACN efficiently using high cofactor concentration and heat. Elderberry anthocyanins were semi-purified and caffeic acid (CA) was dissolved in 15% ethanol and diluted with a buffer to achieve ACN:CA molar ratios of 1:50, 1:100, 1:150, and 1:200, then incubated at 65 °C for 5 days. The effect of temperature was tested using ACN samples incubated with or without CA at 25 °C, 50 °C, and 75 °C for 7 days. Compositional changes were monitored using uHPLC-PDA-MS/MS. Higher CA levels seemed to protect pigment integrity, with ACN:CA 1:150 ratio showing the highest tinctorial strength after 48 h. PACN content growth was fastest between 24 and 48 h for all ACN:CA ratios and after 120 h, all ACN had degraded or converted to PACN. PACN formed faster at higher temperatures, reaching ~90% PACN in 24 h and ~100% PACN in 48 h at 75 °C. These results suggest that PACN can form efficiently from elderberry ACN and CA if heated to produce more stable pigments.

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21

Božič, Jelena Topić, Lorena Butinar, Alen Albreht, Irena Vovk, Dorota Korte, and Branka Mozetič Vodopivec. "The impact of Saccharomyces and non-Saccharomyces yeasts on wine colour: A laboratory study of vinylphenolic pyranoanthocyanin formation and anthocyanin cell wall adsorption." LWT 123 (April 2020): 109072. http://dx.doi.org/10.1016/j.lwt.2020.109072.

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22

Monagas, Maria, Carmen Gómez-Cordovés, and Begoña Bartolomé. "Evaluation of different Saccharomyces cerevisiae strains for red winemaking. Influence on the anthocyanin, pyranoanthocyanin and non-anthocyanin phenolic content and colour characteristics of wines." Food Chemistry 104, no. 2 (January 2007): 814–23. http://dx.doi.org/10.1016/j.foodchem.2006.12.043.

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23

Lu, Yinrong, L. Yeap Foo, and Yan Sun. "New pyranoanthocyanins from blackcurrant seeds." Tetrahedron Letters 43, no. 41 (October 2002): 7341–44. http://dx.doi.org/10.1016/s0040-4039(02)01721-5.

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24

Mateus, Nuno, Joana Oliveira, Mafalda Haettich-Motta, and Victor de Freitas. "New Family of Bluish Pyranoanthocyanins." Journal of Biomedicine and Biotechnology 2004, no. 5 (2004): 299–305. http://dx.doi.org/10.1155/s1110724304404033.

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The use of anthocyanins has been investigated for the preparation of food and beverage natural colorants as they seem to have nontoxic effects. In this context, vinylpyranoanthocyanins were recently found to naturally occur in ageing red wine. This new family of anthocyanin-derived pigments may be obtained directly through the reaction between anthocyanin derivatives and other compounds. Some of these newly formed pigments have been found to exhibit a bluish color at acidic pH. The formation of bluish pigment was obtained through reaction between anthocyanin-pyruvic-acid adducts and flavanols in the presence of acetaldehyde. The formation of similar bluish pigments was attempted using other different precursors. The chromatic features of this kind of pigments bring promising expectations concerning the use of these naturally occurring blue pigments in the food industry.

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25

Lu, Yinrong, Yan Sun, and L. Yeap Foo. "Novel pyranoanthocyanins from black currant seed." Tetrahedron Letters 41, no. 31 (July 2000): 5975–78. http://dx.doi.org/10.1016/s0040-4039(00)00954-0.

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26

Pan, Fengguang, Yanjun Liu, Jingbo Liu, and Erlei Wang. "Stability of blueberry anthocyanin, anthocyanidin and pyranoanthocyanidin pigments and their inhibitory effects and mechanisms in human cervical cancer HeLa cells." RSC Advances 9, no. 19 (2019): 10842–53. http://dx.doi.org/10.1039/c9ra01772k.

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27

Rein, Maarit J., Velimatti Ollilainen, Mikko Vahermo, Jari Yli-Kauhaluoma, and Marina Heinonen. "Identification of novel pyranoanthocyanins in berry juices." European Food Research and Technology 220, no. 3-4 (November 11, 2004): 239–44. http://dx.doi.org/10.1007/s00217-004-1063-6.

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28

Topić Božič, Jelena, Dorota Korte, Branka Mozetič Vodopivec, and Lorena Butinar. "Yeasts and wine colour." Croatian journal of food science and technology 11, no. 2 (November 29, 2019): 291–302. http://dx.doi.org/10.17508/cjfst.2019.11.2.17.

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Historically, yeasts from the genus Saccharomyces have been conventionally used in the production of wine and other fermented beverages. Traditionally, their main role has been the transformation of sugars into ethanol, however, research has shown that yeasts also influence wine aroma, texture, flavour and colour. In lieu of this, non-Saccharomyces yeasts, which have been considered as spoilage yeasts in the past, have been exploited as potential wine starters because they can improve the sensorial characteristics of wines. Because they are considered to be poor fermenters, mixed fermentations with Saccharomyces yeasts are applied either in a form of co-inoculation or sequential fermentation. Among wine characteristics, colour of red wines has special importance because it is the first wine characteristic perceived by the consumers. Red wine colour stems from anthocyanins, located in the grape skins that are extracted to grape must during maceration/fermentation. Various technological strategies in the winemaking process have already been employed to improve wine colour. One of them is yeast-mediated colour improvement employing a careful selection of yeast starters that can promote the synthesis of stable colour pigments pyranoanthocyanins from anthocyanins. The two most known groups of pyranoanthocyanins are vinylphenolic pyranoanthocyanins and vitisins. In comparison to anthocyanins they are less susceptible to pH, SO2 bleaching and oxygen presence. Their concentration in the wines differs according to the yeast strain used and the type of fermentation applied. Furthermore, wine colour can also be influenced by the cell wall adsorption capability of yeasts. Numerous studies have shown the positive influence of a careful selection of non-Saccharomyces yeast in promoting stable pigments synthesis in the production of wine. In this review, we discuss how application of different yeast species – Saccharomyces and non-Saccharomyces can enhance wine colour through different fermentation strategies applied

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29

Akdemir, Hulya, Adilson Silva, Jian Zha, Dmitri V. Zagorevski, and Mattheos A. G. Koffas. "Production of pyranoanthocyanins using Escherichia coli co-cultures." Metabolic Engineering 55 (September 2019): 290–98. http://dx.doi.org/10.1016/j.ymben.2019.05.008.

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30

Leopoldini, Monica, Francesca Rondinelli, Nino Russo, and Marirosa Toscano. "Pyranoanthocyanins: A Theoretical Investigation on Their Antioxidant Activity." Journal of Agricultural and Food Chemistry 58, no. 15 (August 11, 2010): 8862–71. http://dx.doi.org/10.1021/jf101693k.

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31

Freitas, Adilson A., Cassio Pacheco Silva, Gustavo Thalmer M. Silva, António L. Maçanita, and Frank H. Quina. "From vine to wine: photophysics of a pyranoflavylium analog of red wine pyranoanthocyanins." Pure and Applied Chemistry 89, no. 12 (November 27, 2017): 1761–67. http://dx.doi.org/10.1515/pac-2017-0411.

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AbstractIn the ground state, the p-methoxyphenyl-substituted pyranoflavylium cation I, prepared by the reaction of the 5,7-dihydroxy-4-methylflavylium cation with p-methoxybenzaldehyde, is a weak acid (pKa=3.7±0.1). In its lowest excited singlet state, I is a moderate photoacid (pKa*=0.67) in 30% methanol-water acidified with trifluoroacetic acid (TFA). In comparison to anthocyanins and 7-hydroxyflavylium cations, the photoacidity of I is much less pronounced and the rate of proton loss from the excited acid form of I much slower (by a factor of up to 100). In 50% ethanol:0.10 mol dm−3 HClO4, the excited state of the acid form of I undergoes fast (12 ps) initial relaxation (potentially in the direction of an intramolecular charge transfer state), followed by much slower (340 ps) adiabatic deprotonation to form the excited base. The excited base in turn exhibits a moderately fast relaxation (70 ps), consistent with solvent hydrogen-bond reorganization times, followed by slower but efficient decay (1240 ps) back to the ground state. As in uncomplexed anthocyanins and 7-hydroxyflavylium cations, the photophysical behavior of I points to excited state proton transfer as the dominant excited state deactivation pathway of pyranoanthocyanins, consistent with relatively good photostability of natural pyranoanthocyanins.

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32

Quaglieri, Cindy, Gianmarco Iachetti, Michael Jourdes, Pierre Waffo-Teguo, and Pierre-Louis Teissedre. "Are pyranoanthocyanins involved in sensory effect in red wines?" BIO Web of Conferences 7 (2016): 02007. http://dx.doi.org/10.1051/bioconf/20160702007.

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33

Alcalde-Eon, C., M. T. Escribano-Bailón, C. Santos-Buelga, and J. C. Rivas-Gonzalo. "Separation of pyranoanthocyanins from red wine by column chromatography." Analytica Chimica Acta 513, no. 1 (June 2004): 305–18. http://dx.doi.org/10.1016/j.aca.2003.10.076.

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34

Farr, Jacob, and M. Giusti. "Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins." Molecules 23, no. 4 (March 23, 2018): 744. http://dx.doi.org/10.3390/molecules23040744.

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35

Rentzsch, Michael, Michael Schwarz, and Peter Winterhalter. "Pyranoanthocyanins – an overview on structures, occurrence, and pathways of formation." Trends in Food Science & Technology 18, no. 10 (October 2007): 526–34. http://dx.doi.org/10.1016/j.tifs.2007.04.014.

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36

Jordheim, Monica, Kjersti Aaby, Torgils Fossen, Grete Skrede, and Øyvind M. Andersen. "Molar Absorptivities and Reducing Capacity of Pyranoanthocyanins and Other Anthocyanins." Journal of Agricultural and Food Chemistry 55, no. 26 (December 2007): 10591–98. http://dx.doi.org/10.1021/jf071417s.

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37

Azevedo, Joana, Joana Oliveira, Luis Cruz, Natércia Teixeira, Natércia F. Brás, Victor De Freitas, and Nuno Mateus. "Antioxidant Features of Red Wine Pyranoanthocyanins: Experimental and Theoretical Approaches." Journal of Agricultural and Food Chemistry 62, no. 29 (January 14, 2014): 7002–9. http://dx.doi.org/10.1021/jf404735j.

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38

Oliveira, Joana, Nuno Mateus, and Victor de Freitas. "Previous and recent advances in pyranoanthocyanins equilibria in aqueous solution." Dyes and Pigments 100 (January 2014): 190–200. http://dx.doi.org/10.1016/j.dyepig.2013.09.009.

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39

Pozo-Bayón, M. Ángeles, María Monagas, M. Carmen Polo, and Carmen Gómez-Cordovés. "Occurrence of Pyranoanthocyanins in Sparkling Wines Manufactured with Red Grape Varieties." Journal of Agricultural and Food Chemistry 52, no. 5 (March 2004): 1300–1306. http://dx.doi.org/10.1021/jf030639x.

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40

Schwarz, Michael, and Peter Winterhalter. "A novel synthetic route to substituted pyranoanthocyanins with unique colour properties." Tetrahedron Letters 44, no. 41 (October 2003): 7583–87. http://dx.doi.org/10.1016/j.tetlet.2003.08.065.

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41

Muselík, Jan, María García-Alonso, María Martín-López, Milan Žemlička, and Julián Rivas-Gonzalo. "Measurement of Antioxidant Activity of Wine Catechins, Procyanidins, Anthocyanins and Pyranoanthocyanins." International Journal of Molecular Sciences 8, no. 8 (August 14, 2007): 797–809. http://dx.doi.org/10.3390/i8080797.

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42

Carvalho, Alexandre R. F., Joana Oliveira, Victor de Freitas, Nuno Mateus, and André Melo. "A theoretical interpretation of the color of two classes of pyranoanthocyanins." Journal of Molecular Structure: THEOCHEM 948, no. 1-3 (May 2010): 61–64. http://dx.doi.org/10.1016/j.theochem.2010.02.020.

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43

Freitas, Adilson A., Cassio Pacheco Silva, Gustavo Thalmer M. Silva, António L. Maçanita, and Frank H. Quina. "Ground- and Excited-State Acidity of Analogs of Red Wine Pyranoanthocyanins,." Photochemistry and Photobiology 94, no. 6 (June 22, 2018): 1086–91. http://dx.doi.org/10.1111/php.12944.

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44

Gómez-Alonso, Sergio, Dora Blanco-Vega, M. Victoria Gómez, and Isidro Hermosín-Gutiérrez. "Synthesis, Isolation, Structure Elucidation, and Color Properties of 10-Acetyl-pyranoanthocyanins." Journal of Agricultural and Food Chemistry 60, no. 49 (November 30, 2012): 12210–23. http://dx.doi.org/10.1021/jf303854u.

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45

García-Estévez, Ignacio, Luís Cruz, Joana Oliveira, Nuno Mateus, Victor de Freitas, and Susana Soares. "First evidences of interaction between pyranoanthocyanins and salivary proline-rich proteins." Food Chemistry 228 (August 2017): 574–81. http://dx.doi.org/10.1016/j.foodchem.2017.02.030.

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46

Phan, Kim, Steven De Meester, Katleen Raes, Karen De Clerck, and Veronique Van Speybroeck. "A Comparative Study on the Photophysical Properties of Anthocyanins and Pyranoanthocyanins." Chemistry – A European Journal 27, no. 19 (March 3, 2021): 5956–71. http://dx.doi.org/10.1002/chem.202004639.

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47

Marquez, Ana, Montserrat Dueñas, María P. Serratosa, and Julieta Merida. "Identification by HPLC-MS of Anthocyanin Derivatives in Raisins." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/274893.

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The anthocyanin composition in red grapes dried under controlled conditions has been studied. Pyranoanthocyanins and condensed anthocyanins with flavanols by a methylmethine bridge have been identified. Typically, these compounds appear in wine after the fermentation process, as they require compounds such as pyruvic acid, acetoacetic acid, and acetaldehyde for their formation. During the chamber-drying process a stress situation is originated, inducing significant changes in the grape metabolism from aerobic to anaerobic, and as a result it produces the activation of the alcohol dehydrogenase enzyme (ADH) and others that would cause the formation of these compounds. These derivatives are very interesting because they give greater stability to the color of red wine.

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48

Schwarz, Michael, Victor Wray, and Peter Winterhalter. "Isolation and Identification of Novel Pyranoanthocyanins from Black Carrot (Daucus carotaL.) Juice." Journal of Agricultural and Food Chemistry 52, no. 16 (August 2004): 5095–101. http://dx.doi.org/10.1021/jf0495791.

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49

Oliveira, Joana, Nuno Mateus, and Victor de Freitas. "ChemInform Abstract: Previous and Recent Advances in Pyranoanthocyanins Equilibria in Aqueous Solution." ChemInform 45, no. 7 (January 31, 2014): no. http://dx.doi.org/10.1002/chin.201407263.

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50

Morata, A., S. Benito, I. Loira, F. Palomero, M. C. González, and J. A. Suárez-Lepe. "Formation of pyranoanthocyanins by Schizosaccharomyces pombe during the fermentation of red must." International Journal of Food Microbiology 159, no. 1 (September 2012): 47–53. http://dx.doi.org/10.1016/j.ijfoodmicro.2012.08.007.

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