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Phytoalexins: Current Progress and Future Prospects Edited by Philippe Jeandet Printed Edition of the Special Issue Published in Molecules www.mdpi.com/journal/molecules Philippe Jeandet (Ed.) Phytoalexins: Current Progress and Future Prospects This book is a reprint of the special issue that appeared in the online open access journal Molecules (ISSN 1420-3049) in 2014 (available at: http://www.mdpi.com/journal/molecules/special_issues/phytoalexins-progress). Guest Editor Philippe Jeandet Laboratory of Stress, Defenses and Plant Reproduction U.R.V.V.C., UPRES EA 4707, Faculty of Sciences, University of Reims, PO Box. 1039, 51687 Reims cedex 02, France Editorial Office MDPI AG Klybeckstrasse 64 Basel, Switzerland Publisher Shu-Kun Lin Managing Editor Ran Dang 1. Edition 2015 MDPI • Basel • Beijing ISBN 978-3-03842-059-0 © 2015 by the authors; licensee MDPI, Basel, Switzerland. All articles in this volume are Open Access distributed under the Creative Commons Attribution 3.0 license (http://creativecommons.org/licenses/by/3.0/), which allows users to download, copy and build upon published articles even for commercial purposes, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. However, the dissemination and distribution of copies of this book as a whole is restricted to MDPI, Basel, Switzerland. III Table of Contents About the Editor ............................................................................................................... VII List of Contributors ......................................................................................................... VIII Editorial - Philippe Jeandet Phytoalexins: Current Progress and Future Prospects Reprinted from: Molecules 2015, 20, 2770-2774 http://www.mdpi.com/1420-3049/20/2/2770 .......................................................................... 1 Philippe Jeandet, Claire Hébrard, Marie-Alice Deville, Sylvain Cordelier, Stéphan Dorey, Aziz Aziz and Jérôme Crouzet Deciphering the Role of Phytoalexins in Plant-Microorganism Interactions and Human Health Reprinted from: Molecules 2014, 19, 18033–18056 http://www.mdpi.com/1420-3049/19/11/18033 ...................................................................... 6 Alana Poloni and Jan Schirawski Red Card for Pathogens: Phytoalexins in Sorghum and Maize Reprinted from: Molecules 2014, 19, 9114–9133 http://www.mdpi.com/1420-3049/19/7/9114 ........................................................................ 30 Yinning Chen, Tao Yan, Chenghai Gao, Wenhao Cao and Riming Huang Natural Products from the Genus Tephrosia Reprinted from: Molecules 2014, 19, 1432–1458 http://www.mdpi.com/1420-3049/19/2/1432 ........................................................................ 50 Magda Formela, Sławomir Samardakiewicz, Łukasz Marczak, Witold Nowak, Dorota Narożna, Waldemar Bednarski, Anna Kasprowicz-Maluśki and Iwona Morkunas Effects of Endogenous Signals and Fusarium oxysporum on the Mechanism Regulating Genistein Synthesis and Accumulation in Yellow Lupine and Their Impact on Plant Cell Cytoskeleton Reprinted from: Molecules 2014, 19, 13392–13421 http://www.mdpi.com/1420-3049/19/9/13392 ...................................................................... 77 IV Olga V. Zernova, Anatoli V. Lygin, Michelle L. Pawlowski, Curtis B. Hill, Glen L. Hartman, Jack M. Widholm and Vera V. Lozovaya Regulation of Plant Immunity through Modulation of Phytoalexin Synthesis Reprinted from: Molecules 2014, 19, 7480–7496 http://www.mdpi.com/1420-3049/19/6/7480 ...................................................................... 114 Farag Ibraheem, Iffa Gaffoor, Qixian Tan, Chi-Ren Shyu and Surinder Chopra A Sorghum MYB Transcription Factor Induces 3-Deoxyanthocyanidins and Enhances Resistance against Leaf Blights in Maize Reprinted from: Molecules 2015, 20, 2388–2404 http://www.mdpi.com/1420-3049/20/2/2388 ...................................................................... 131 Lee A. Hadwiger and Kiwamu Tanaka EDTA a Novel Inducer of Pisatin, a Phytoalexin Indicator of the Non-Host Resistance in Peas Reprinted from: Molecules 2015, 20, 24–34 http://www.mdpi.com/1420-3049/20/1/24 .......................................................................... 149 Simona M. Sanzani, Leonardo Schena and Antonio Ippolito Effectiveness of Phenolic Compounds against Citrus Green Mould Reprinted from: Molecules 2014, 19, 12500–12508 http://www.mdpi.com/1420-3049/19/8/12500 .................................................................... 160 Morifumi Hasegawa, Ichiro Mitsuhara, Shigemi Seo, Kazunori Okada, Hisakazu Yamane, Takayoshi Iwai and Yuko Ohashi Analysis on Blast Fungus-Responsive Characters of a Flavonoid Phytoalexin Sakuranetin; Accumulation in Infected Rice Leaves, Antifungal Activity and Detoxification by Fungus Reprinted from: Molecules 2014, 19, 11404–11418 http://www.mdpi.com/1420-3049/19/8/11404 .................................................................... 169 Malik Chalal, Agnès Klinguer, Abdelwahad Echairi, Philippe Meunier, Dominique Vervandier-Fasseur and Marielle Adrian Antimicrobial Activity of Resveratrol Analogues Reprinted from: Molecules 2014, 19, 7679–7688 http://www.mdpi.com/1420-3049/19/6/7679 ...................................................................... 184 V Yangrae Cho, Robin A. Ohm, Rakshit Devappa, Hyang Burm Lee, Igor V. Grigoriev, Bo Yeon Kim and Jong Seog Ahn Transcriptional Responses of the Bdtf1-Deletion Mutant to the Phytoalexin Brassinin in the Necrotrophic Fungus Alternaria brassicicola Reprinted from: Molecules 2014, 19, 10717–10732 http://www.mdpi.com/1420-3049/19/8/10717 .................................................................... 193 Loïc Becker, Vincent Carré, Anne Poutaraud, Didier Merdinoglu and Patrick Chaimbault MALDI Mass Spectrometry Imaging for the Simultaneous Location of Resveratrol, Pterostilbene and Viniferins on Grapevine Leaves Reprinted from: Molecules 2014, 19, 10587–10600 http://www.mdpi.com/1420-3049/19/7/10587 .................................................................... 372 Guillaume Marti, Sylvain Schnee, Yannis Andrey, Claudia Simoes-Pires, Pierre-Alain Carrupt, Jean-Luc Wolfender and Katia Gindro Study of Leaf Metabolome Modifications Induced by UV-C Radiations in Representative Vitis, Cissus and Cannabis Species by LC-MS Based Metabolomics and Antioxidant Assays Reprinted from: Molecules 2014, 19, 14004–14021 http://www.mdpi.com/1420-3049/19/9/14004 .................................................................... 386 Glòria Lozano-Mena, Marta Sánchez-González, M. Emília Juan and Joana M. Planas Maslinic Acid, a Natural Phytoalexin-Type Triterpene from Olives — A Promising Nutraceutical? Reprinted from: Molecules 2014, 19, 11538–11559 http://www.mdpi.com/1420-3049/19/8/11538 .................................................................... 404 Martin Kello, David Drutovic, Martina Chripkova, Martina Pilatova, Mariana Budovska, Lucia Kulikova, Peter Urdzik and Jan Mojzis ROS-Dependent Antiproliferative Effect of Brassinin Derivative Homobrassinin in Human Colorectal Cancer Caco2 Cells Reprinted from: Molecules 2014, 19, 10877–10897 http://www.mdpi.com/1420-3049/19/8/10877 .................................................................... 426 VI Basil Smith, Diandra Randle, Roman Mezencev, LeeShawn Thomas, Cimona Hinton and Valerie Odero-Marah Camalexin-Induced Apoptosis in Prostate Cancer Cells Involves Alterations of Expression and Activity of Lysosomal Protease Cathepsin D Reprinted from: Molecules 2014, 19, 3988–4005 http://www.mdpi.com/1420-3049/19/4/3988 ...................................................................... 447 Audrey E. McCalley, Simon Kaja, Andrew J. Payne and Peter Koulen Resveratrol and Calcium Signaling: Molecular Mechanisms and Clinical Relevance Reprinted from: Molecules 2014, 19, 7327–7340 http://www.mdpi.com/1420-3049/19/6/7327 ...................................................................... 466 Malik Chalal, Dominique Delmas, Philippe Meunier, Norbert Latruffe and Dominique Vervandier-Fasseur Inhibition of Cancer Derived Cell Lines Proliferation by Synthesized Hydroxylated Stilbenes and New Ferrocenyl-Stilbene Analogs. Comparison with Resveratrol Reprinted from: Molecules 2014, 19, 7850–7868 http://www.mdpi.com/1420-3049/19/6/7850 ...................................................................... 480 VII About the Editor Philippe Jeandet received his doctorates in plant physiology and biochemistry in 1991 and 1996 from the University of Bourgogne (France). He started his research activities on resveratrol, a phytoalexin from the Vitaceae produced in response to fungal attacks or injury. He received an associate professor position at the University of Bourgogne (1993-1997). In 1997, Philippe Jeandet accepted a position as a professor and chairman of the laboratory of oenology and applied chemistry at the University of Reims. His research activities focussed on physico-chemistry applied to wine and microbiology. He has been respectively the director (2003-2008) and adjunct director (2008-2013) of the research unit vine and wine of Champagne and adjunct to the director of research and technology in the Champagne- Ardennes area (2004-2010). He is now co-leader of a research team on resveratrol at the laboratory of stress, defences and plant reproduction and member of the council of the Georges Chappaz research institute of vine and wine of Champagne. He has published over 250 papers in referred Journals
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  • Isoflavonoid Biosynthesis 21321.Pdf

    Isoflavonoid Biosynthesis 21321.Pdf

    Isoflavonoid Biosynthesis https://www.kegg.jp/kegg-bin/highlight_pathway?scale=1.0&map=map00943&keyword=flavonoids Isoflavonoids are biologically active compounds, such as phytoestrogens, produced by pea family plants. While flavonoids (in the narrow sense) have the 2- phenylchromen-4-one backbone, isoflavonoids have the 3-phenylchromen-4-one backbone with no hydroxyl group substitution at position 2. Isoflavonoids are derived from the flavonoid biosynthesis pathway via liquiritigenin or naringenin. (Flavonoid Biosynthesis) -> [1,2] 1) Liquiritigenin -> [1,2,3] 1) flavone synthesis I & II -> 7,4’Dihydroxyflavone OR 2) flavonoid 6-hydroxylase -> 6,7,4’-Trihydroxyflavanone -> 2- hydroxyisoflavone synthase -> 2,6,7,4’-tetrahydroxyisoflavanone -> 6- Hydroxydaidzein -> Glycitein -> isoflavone 7-O-glucosyltransferase -> Glycitein 7-O-glucoside -> isoflavone 7-O-glucoside-6’’-O-malonyltransferase -> Glycitein 7-O-glucoside-6”-O-malonate OR 3) 2-hydroxyisoflavanone synthase -> 2,7,4’Trihydroxyisoflavanone -> [1,2] 1) Feedback Loop 2,7,4’-trihydroxyisoflavanone 4’-O-methyltransferase / isoflavone 4’-O-methyltransferase -> 2,7-Dihydroxy-4’-methoxyisoflavanone -> 2- hydroxyisoflavanone dehydratase -> Formononetin OR 2) 2-hydroxyisoflavone dehydratase -> Daidzein -> [1,2,3,4,5] 1) isoflavone/4’-methoxyisoflavone 2’-hydroxylase -> 2’Hydroxydaidzein -> 2’Hydroxydaidzein reductase -> 2’-Hydroxydihydrodaidzein -> 3,9-Dihydroxypterocarpan -> 3,9-dihydroxypterocarpan 6a-monooxygenase -> 3,6,9- Trihydroxypterocarpan -> [1,2] 1) trihydroxypterocarpan dimethylallyltransferase