History of Chemical Routes towards Cyclic Non-Enzymatic Oxygenated Metabolites of Polyunsaturated Fatty Acids

• Published in: Synthesis (Stuttgart) 2018-09, Vol.50 (17), p.3257-3280
• Main Authors: Oger, Camille, Cuyamendous, Claire, de la Torre, Aurélien, Candy, Mathieu, Guy, Alexandre, Bultel-Poncé, Valérie, Durand, Thierry, Galano, Jean-Marie
• Format: Article
• Language: English
• Subjects: Chemical Sciences; review
• ISSN: 0039-7881; 1437-210X
• DOI: 10.1055/s-0036-1589540

Abstract Enzymatically formed oxygenated metabolites of polyunsaturated fatty acids (PUFA) are of great interest for the scientific community being mediators and biomarkers in the physiological and pathological regulation of many key biological processes. More recently; metabolites of PUFA formed through a non-enzymatic free radical pathway have gained interest in diseases linked with oxidative stress. Thus, synthetic strategies leading to the total synthesis of such metabolites are an essential field of research, and this review will cover a structural presentation, will discuss their biological interests, and present total syntheses reported between 2008 and 2017. 1 Introduction 2 Non-Enzymatic Metabolites of PUFAs 2.1 Where Do They Come From? 2.2 Why Are They Interesting Metabolites? 2.3 A Huge Family of Natural Compounds 2.3.1 Presentation of All Families 2.3.1.1 Isoprostanoids 2.3.1.2 Isofuranoids 2.3.1.3 Isoketals 2.3.2 Nomenclature of These Metabolites 2.3.2.1 Isoprostanoids 2.3.2.2 Isofuranoids 2.3.2.3 Isoketals 3 Total Synthesis Strategies 3.1 Isoprostanoids 3.2 Isofuranoids 3.3 Isoketals 4 The Discoveries Behind the Synthesis 4.1 Recent Identification and Biomarkers Roles of Isoprostanes and Isofuranes 4.2 Biological Properties 4.2.1 Phytoprostanes, Isoprostanes, and Neuroprostanes 4.2.2 Epoxy-isoprostanes 5 Conclusion