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Free Radical Research Volume 39, 2005 - Issue 5
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Original Article

Natural and newly synthesized hydroxy-1-aryl-isochromans: A class of potential antioxidants and radical scavengers

Peter Lorenz Institute for Medical Neurobiology, Otto-von-Guericke University, Leipziger Strasse 44, D-39120, Magdeburg, GermanyCorrespondence[email protected]
,
Michael Zeh Institute for Medical Neurobiology, Otto-von-Guericke University, Leipziger Strasse 44, D-39120, Magdeburg, Germany
,
Jens Martens-Lobenhoffer Institute for Clinical Pharmacology, Otto-von-Guericke University, Leipziger Strasse 44, D-39120, Magdeburg, Germany
,
Harry Schmidt Institute of Inorganic Chemistry, Martin Luther University Halle-Wittenberg, Kurt-Mothes-Strasse 2, D-06120, Halle/Saale, Germany
,
Gerald Wolf Institute for Medical Neurobiology, Otto-von-Guericke University, Leipziger Strasse 44, D-39120, Magdeburg, Germany
&
Thomas F.W. Horn Institute for Medical Neurobiology, Otto-von-Guericke University, Leipziger Strasse 44, D-39120, Magdeburg, GermanyCorrespondence[email protected]
Pages 535-545 | Received 02 Sep 2004, Published online: 07 Jul 2009

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Wonmin Ko, Tran Hong Quang, Jae Hak Sohn, Joung Han Yim, Dae Gill Kang, Ho Sub Lee, Youn-Chul Kim & Hyuncheol Oh. (2019) Anti-inflammatory effect of 3,7-dimethyl-1,8-hydroxy-6-methoxyisochroman via nuclear factor erythroid 2-like 2-mediated heme oxygenase-1 expression in lipopolysaccharide-stimulated RAW264.7 and BV2 cells. Immunopharmacology and Immunotoxicology 41:2, pages 337-348.
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Dan-Yi Li, Jin-Xia Wei, Hui-Ming Hua & Zhan-Lin Li. (2014) Antimicrobial constituents from the flowers of Trollius chinensis. Journal of Asian Natural Products Research 16:10, pages 1018-1023.
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Marcella Guiso, Carolina Marra & Francesco Piccioni. (2010) DDQ oxidation of hydroxyisochromans and homologues. Natural Product Research 24:4, pages 331-340.
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Marcella Guiso, Carolina Marra & Rocio Rodriguez Arcos. (2008) An investigation on dihydroxy-isochromans in extra virgin olive oil. Natural Product Research 22:16, pages 1403-1409.
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Michael Zeh, Peter Lorenz, Peter Kreutzmann & Peter Schönfeld. (2008) Hydroxy-1-aryl-isochromans: protective compounds against lipid peroxidation and cellular nitrosative stress. Redox Report 13:1, pages 23-30.
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Articles from other publishers (27)

Lilo K. Mailänder, Peter Lorenz, Hannes Bitterling, Florian C. Stintzing, Rolf Daniels & Dietmar R. Kammerer. (2022) Phytochemical Characterization of Chamomile (Matricaria recutita L.) Roots and Evaluation of Their Antioxidant and Antibacterial Potential. Molecules 27:23, pages 8508.
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Meng-Yang Chang, Shin-Mei Chen & Yu-Ting Hsiao. (2019) Trifluoroacetic Anhydride Mediated One-Pot Synthesis of 1-Aryl Isochroman-3-ones via the Carboxy-Pictet–Spengler Reaction. The Journal of Organic Chemistry 84:18, pages 11687-11698.
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Luca Lombardo, Filomena Grasso, Francesca Lanciano, Stefania Loria & Emanuela Monetti. 2018. 41 77 .
Gianluigi Albano & Laura Antonella Aronica. (2017) Potentiality and Synthesis of O- and N-Heterocycles: Pd-Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines. European Journal of Organic Chemistry 2017:48, pages 7204-7221.
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Aamer Saeed & Amara Mumtaz. (2017) Novel isochroman-triazoles and thiadiazole hybrids: Design, synthesis and antimicrobial activity. Journal of Saudi Chemical Society 21:2, pages 186-192.
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Andrea Temperini, Anna Barattucci, Paola Maria Bonaccorsi, Ornelio Rosati & Lucio Minuti. (2015) Stereoselective Synthesis of Substituted Tetrahydropyrans and Isochromans by Cyclization of Phenylseleno Alcohols. The Journal of Organic Chemistry 80:16, pages 8102-8112.
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Raquel Mateos, Andrés Madrona, Gema Pereira-Caro, Vanessa Domínguez, Rosa M.a Cert, Juan Parrado, Beatriz Sarriá, Laura Bravo & José Luis Espartero. (2015) Synthesis and antioxidant evaluation of isochroman-derivatives of hydroxytyrosol: Structure–activity relationship. Food Chemistry 173, pages 313-320.
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Rosa Cert, Andrés Madrona, José Luis Espartero & M. Carmen Pérez-Camino. (2015) Antioxidant activity of alkyl hydroxytyrosyl ethers in unsaturated lipids. Food & Function 6:6, pages 1999-2007.
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Laura Antonella Aronica, Luca Giannotti, Stefano Giuntini & Anna Maria Caporusso. (2014) Synthesis of 2-Alkylideneisochromans by Cyclocarbonylative Sonogashira Reactions. European Journal of Organic Chemistry 2014:31, pages 6858-6862.
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Robert C. Simon, Eduardo Busto, Nina Richter, Ferdinand Belaj & Wolfgang Kroutil. (2013) Chemoenzymatic Synthesis of Enantiomerically Pure syn ‐Configured 1‐Aryl‐3‐methylisochroman Derivatives . European Journal of Organic Chemistry 2014:1, pages 111-121.
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Robert J. Hinkle & Shane E. Lewis. (2013) Atom Economical, One-Pot, Three-Reaction Cascade to Novel Tricyclic 2,4-Dihydro-1 H -benzo[ f ]isochromenes . Organic Letters 15:16, pages 4070-4073.
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A. Guerrero, J.P. De La Cruz, J. Muñoz-Marín, J.A. López-Villodres, A. Madrona, J.L. Espartero & J.A. González-Correa. (2012) Neuroprotective effect of alkyl hydroxytyrosyl ethers in rat brain slices subjected to a hypoxia-reoxygenation model. Food Chemistry 134:4, pages 2176-2183.
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Yong-Ming Yan, Huan-Qin Dai, Yuhong Du, Bernd Schneider, Hui Guo, Dian-Peng Li, Li-Xin Zhang, Haian Fu, Xiao-Ping Dong & Yong-Xian Cheng. (2012) Identification of blapsins A and B as potent small-molecule 14-3-3 inhibitors from the insect Blaps japanensis. Bioorganic & Medicinal Chemistry Letters 22:12, pages 4179-4181.
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Soo J. Park, Jason R. Price & Matthew H. Todd. (2011) Oxidative Arylation of Isochroman. The Journal of Organic Chemistry 77:2, pages 949-955.
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Enrique L. Larghi & Teodoro S. Kaufman. (2011) Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects. European Journal of Organic Chemistry 2011:27, pages 5195-5231.
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Giuliana Trefiletti, Anna Rita Togna, Valentina Latina, Carolina Marra, Marcella Guiso & Giuseppina I. Togna. (2011) 1-Phenyl-6,7-dihydroxy-isochroman suppresses lipopolysaccharide-induced pro-inflammatory mediator production in human monocytes. British Journal of Nutrition 106:1, pages 33-36.
Crossref
Won-Seok Choi, Jae-Whang Lee, Yun-Gi Cho & Nack-Do Sung. (2010) The Influence of the Substituents on the Benzo Ring for Antioxidant Activity of 4-Methyl-2H-benzopyran-2-one Analogues. Journal of Applied Biological Chemistry 53:2, pages 99-104.
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Aamer Saeed. (2010) Oxa-Pictet–Spengler reaction in water. Synthesis of some (±)-1-aryl-6,7-dimethoxyisochromans. Chinese Chemical Letters 21:3, pages 261-264.
Crossref
Peter Schönfeld, Nicol Kruska & Georg Reiser. (2009) Antioxidative activity of the olive oil constituent hydroxy-1-aryl-isochromans in cells and cell-free systems. Biochimica et Biophysica Acta (BBA) - General Subjects 1790:12, pages 1698-1704.
Crossref
Andrés Madrona, Gema Pereira-Caro, Raquel Mateos, Guillermo Rodríguez, Mariana Trujillo, Juan Fernández-Bolaños & José Espartero. (2009) Synthesis of Hydroxytyrosyl Alkyl Ethers from Olive Oil Waste Waters. Molecules 14:5, pages 1762-1772.
Crossref
Aamer Saeed, Jim Simpson & Roderick G. Stanley. (2009) 1-(2-Fluorophenyl)-6,7-dimethoxyisochroman. Acta Crystallographica Section E Structure Reports Online 65:4, pages o867-o868.
Crossref
Aamer SAEED & Amara MUMTAZ. (2008) Microwave‐accelerated Synthesis of Some (±)‐1‐Aryl‐5‐chloroisochromans. Chinese Journal of Chemistry 26:9, pages 1647-1650.
Crossref
Marcella Guiso, Giuliana Trefiletti & Giuseppina Togna. 2008. Olive Oil. Olive Oil 193 200 .
Dimitrios Boskou. 2008. Olive Oil. Olive Oil 11 44 .
Yuan-Ching Chang, Fu-Wei Lee, Chien-Shu Chen, Sheng-Tung Huang, Shin-Hui Tsai, Shih-Hao Huang & Chun-Mao Lin. (2007) Structure-activity relationship of C6-C3 phenylpropanoids on xanthine oxidase-inhibiting and free radical-scavenging activities. Free Radical Biology and Medicine 43:11, pages 1541-1551.
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Alessandra Bendini, Lorenzo Cerretani, Alegria Carrasco-Pancorbo, Ana Gómez-Caravaca, Antonio Segura-Carretero, Alberto Fernández-Gutiérrez & Giovanni Lercker. (2007) Phenolic Molecules in Virgin Olive Oils: a Survey of Their Sensory Properties, Health Effects, Antioxidant Activity and Analytical Methods. An Overview of the Last Decade Alessandra. Molecules 12:8, pages 1679-1719.
Crossref
Ngoc-Anh Le. (2006) Hyperlipidaemia and cardiovascular disease: oxidative damage and atherosclerosis. Current Opinion in Lipidology 17:1, pages 92-94.
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