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Advances in Anthocyanin Research 2018 molecules Advances in Anthocyanin Research 2018 Edited by M. Monica Giusti and Gregory T. Sigurdson Printed Edition of the Special Issue Published in Molecules www.mdpi.com/journal/molecules Advances in Anthocyanin Research 2018 Advances in Anthocyanin Research 2018 Special Issue Editors M. Monica Giusti Gregory T. Sigurdson MDPI • Basel • Beijing • Wuhan • Barcelona • Belgrade Special Issue Editors M. Monica Giusti Gregory T. Sigurdson The Ohio State University The Ohio State University USA USA Editorial Office MDPI St. Alban-Anlage 66 4052 Basel, Switzerland This is a reprint of articles from the Special Issue published online in the open access journal Molecules (ISSN 1420-3049) in 2018 (available at: https://www.mdpi.com/journal/molecules/special issues/ anthocyanin) For citation purposes, cite each article independently as indicated on the article page online and as indicated below: LastName, A.A.; LastName, B.B.; LastName, C.C. Article Title. Journal Name Year, Article Number, Page Range. ISBN 978-3-03897-523-6 (Pbk) ISBN 978-3-03897-524-3 (PDF) c 2019 by the authors. Articles in this book are Open Access and distributed under the Creative Commons Attribution (CC BY) license, which allows users to download, copy and build upon published articles, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. The book as a whole is distributed by MDPI under the terms and conditions of the Creative Commons license CC BY-NC-ND. Contents About the Special Issue Editors ..................................... vii Preface to ”Advances in Anthocyanin Research 2018” ........................ ix Olivier Dangles and Julie-Anne Fenger The Chemical Reactivity of Anthocyanins and Its Consequences in Food Science and Nutrition Reprinted from: Molecules 2018, 23, 1970, doi:10.3390/molecules23081970 .............. 1 Yali Zhou, Chunlong Yuan, Shicheng Ruan, Zhenwen Zhang, Jiangfei Meng and Zhumei Xi Exogenous 24-Epibrassinolide Interacts with Light to Regulate Anthocyanin and Proanthocyanidin Biosynthesis in Cabernet Sauvignon (Vitis vinifera L.) Reprinted from: Molecules 2018, 23, 93, doi:10.3390/molecules23010093 ............... 24 Zuhaili Yusof, Sujatha Ramasamy, Noor Zalina Mahmood and Jamilah Syafawati Yaacob Vermicompost Supplementation Improves the Stability of Bioactive Anthocyanin and Phenolic Compounds in Clinacanthus nutans Lindau Reprinted from: Molecules 2018, 23, 1345, doi:10.3390/molecules23061345 .............. 42 Sonia Mbarki, Oksana Sytar, Marek Zivcak, Chedly Abdelly, Artemio Cerda and Marian Brestic Anthocyanins of Coloured Wheat Genotypes in Specific Response to SalStress Reprinted from: Molecules 2018, 23, 1518, doi:10.3390/molecules23071518 .............. 55 Pradeep Kumar Sudheeran, Oleg Feygenberg, Dalia Maurer and Noam Alkan Improved Cold Tolerance of Mango Fruit with Enhanced Anthocyanin and Flavonoid Contents Reprinted from: Molecules 2018, 23, 1832, doi:10.3390/molecules23071832 .............. 70 Pavel A. Zykin, Elena A. Andreeva, Anna N. Lykholay, Natalia V. Tsvetkova and Anatoly V. Voylokov Anthocyanin Composition and Content in Rye Plants with Different Grain Color Reprinted from: Molecules 2018, 23, 948, doi:10.3390/molecules23040948 .............. 84 Hai-Yao Wu, Kai-Min Yang and Po-Yuan Chiang Roselle Anthocyanins: Antioxidant Properties and Stability to Heat and pH Reprinted from: Molecules 2018, 23, 1357, doi:10.3390/molecules23061357 .............. 96 Carolina Fredes, Camila Becerra, Javier Parada and Paz Robert The Microencapsulation of Maqui (Aristotelia chilensis (Mol.) Stuntz) Juice by Spray-Drying and Freeze-Drying Produces Powders with Similar Anthocyanin Stability and Bioaccessibility Reprinted from: Molecules 2018, 23, 1227, doi:10.3390/molecules23051227 ..............109 Jacob E. Farr and M. Monica Giusti Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins Reprinted from: Molecules 2018, 23, 744, doi:10.3390/molecules23040744 ..............124 Gregory T. Sigurdson, Peipei Tang and M. M´onicaGiusti Cis–Trans Configuration of Coumaric Acid Acylation Affects the Spectral and Colorimetric Properties of Anthocyanins Reprinted from: Molecules 2018, 23, 598, doi:10.3390/molecules23030598 ..............137 v Ana Selene M´arquez-Rodr´ıguez, Claudia Grajeda-Iglesias, Nora-Ayde´eS´anchez-Bojorge, Mar´ıa-CruzFigueroa-Espinoza, Luz-Mar´ıaRodr´ıguez-Valdez, Mar´ıaElena Fuentes-Montero and Erika Salas Theoretical Characterization by Density Functional Theory (DFT) of Delphinidin 3-O-Sambubioside and Its Esters Obtained by Chemical Lipophilization Reprinted from: Molecules 2018, 23, 1587, doi:10.3390/molecules23071587 ..............151 Oksana Sytar, Paulina Bo´sko,Marek Zivˇˇ c´ak, Marian Brestic and Iryna Smetanska Bioactive Phytochemicals and Antioxidant Properties of the Grains and Sprouts of Colored Wheat Genotypes Reprinted from: Molecules 2018, 23, 2282, doi:10.3390/molecules23092282 ..............167 Naoki Nanashima, Kayo Horie and Hayato Maeda Phytoestrogenic Activity of Blackcurrant Anthocyanins Is Partially Mediated through Estrogen Receptor Beta Reprinted from: Molecules 2018, 23, 74, doi:10.3390/molecules23010074 ...............181 Hu Chen, Wansha Yu, Guo Chen, Shuai Meng, Zhonghuai Xiang and Ningjia He Antinociceptive and Antibacterial Properties of Anthocyanins and Flavonols from Fruits of Black and Non-Black Mulberries Reprinted from: Molecules 2018, 23, 4, doi:10.3390/molecules23010004 ................192 Emily F. Warner, Ildefonso Rodriguez-Ramiro, Maria A. O’Connell and Colin D. Kay Cardiovascular Mechanisms of Action of Anthocyanins May Be Associated with the Impact of Microbial Metabolites on Heme Oxygenase-1 in Vascular Smooth Muscle Cells Reprinted from: Molecules 2018, 23, 898, doi:10.3390/molecules23040898 ..............205 vi About the Special Issue Editors M. Monica Giusti is a Professor and the Graduate Studies Chair at the Food Science and Technology Department, The Ohio State University. She is also a member of the graduate faculty of the Facultad de Industrias Alimentarias, Universidad Nacional Agraria, La Molina, Peru.´ Her research is focused on the chemistry and functionality of flavonoids, with an emphasis on anthocyanins. Together with her collaborators, she investigates polyphenols including their incidence and concentration in plants, stability and interactions with food matrices, novel analytical procedures, and the bioavailability, bio-transformations and potential bioactivity of these wonderful plant pigments. To date, Dr. Giusti’s research has generated 100 peer-reviewed publications and 20 book chapters. She is also the co-editor of three books in the field of anthocyanins, and the co-inventor of six USA and international patents. For her innovative work, she was named the 2010 Ohio Agricultural Research and Development Center Director’s Innovator of the Year, the 2011 TechColumbus Outstanding Woman in Technology, and the 2013 OSU Early Career Innovator of the Year. Dr. Giusti is a member of the American Chemical Society and the Institute of Food Technologists (IFT). Before joining The Ohio State University, Dr. Giusti was a faculty member at the Department of Nutrition and Food Science at the University of Maryland. Dr. Giusti, born in Lima, Peru, received a Food Engineer degree from the Universidad Nacional Agraria, La Molina, Peru as well as Master’s and Doctorate degrees in Food Science from Oregon State University, Corvallis, Oregon. Gregory T. Sigurdson, Ph.D., is a Researcher Scientist and Laboratory Manager of the Phytochemicals Lab at the Department of Food Science and Technology, The Ohio State University, where he obtained his doctorate degree in Food Science and Technology after working as professional chef. His research work has focused on the chemistry and application of flavonoid compounds, with a focus on anthocyanins. His research has included aspects on the evaluation of raw materials for their pigment profiles and concentrations, the isolation of individual pigments from mixed matrices, understanding the role of chemical substitutions in color and reactivity, methods of modifying and stabilizing these hues, and the investigation of plant and human metabolites as well as their relations with health. He has a special interest in the development of naturally derived alternatives for synthetic blue food colorants; his work in the production and stabilization of blue colors produced by anthocyanins has led to applications for two patents. In his young academic career, he has generated 17 peer-reviewed publications and one book chapter and he has presented at international conferences on anthocyanin and natural colorants chemistry. At The Ohio State University, he also serves as coordinator in an initiative that aims to engage undergraduate students in research, called FoodSURE (Food Science Undergraduate Research Experience). vii Preface to ”Advances in Anthocyanin Research 2018” Interest in and research on anthocyanin-based pigments have been increasing considerably in recent years. PubMed shows an almost exponential growth curve in the number of anthocyanins publications, having increased from 55 (in 1996) to 264 (in 2006) and again to 910 (in 2017). Anthocyanins have long been identified as important pigments responsible for many flower, fruit, and vegetable colorations, producing a complex variety of hues ranging from yellow to red to purple to blue. More recently, colorants are being studied, not only for their biochemical roles in plants, but also
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