Feature Phytoprostanes Jacinta Collado-González, Thierry Durand, Federico Ferreres, Sonia Medina, Arturo Torrecillas, Ángel Gil-Izquierdo J.C.-G. is PhD student, F.F. and A.T. are Research Professors, and A.G.-I. Tenured Scientist at CEBAS (CSIC), Department of Food Science and Technology, Research Group on Quality, Safety and Bioactivity of Plant Foods and Department of Irrigation, P.O. Box 164, E-30100 Espinardo, Murcia, Spain. E-mail: angelgil@cebas.csic.es T.D. is a CNRS Researcher Director at Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 – CNRS – University of Montpellier – ENSCM, Faculty of Pharmacy, Montpellier, France Summary Phytoprostanes are non-enzymatic lipid peroxidation products derived from α-linolenic acid. Phytoprostanes are not essential for the meta- bolic activity of living cells but they are considered components of oxidative injury-sensing systems and act as excellent biomarkers of oxida- tive degradation in plant-derived foodstuffs. They can be quickly and accurately quantified by UHPLC/MS-MS. Specific agronomic and industrial practices can enhance the phytoprostanes content of fruits and seeds and derived vegetable oils. In vitro studies have shown positive biological activities of these compounds and according to existing reports they are orally bioavailable. Further studies are required to comprehensively study the bioavailability and physiological effects of the phytoprostanes. Introduction In humans and other mammals, oxidative stress is associated with the pathogenesis of several chronic diseases. High levels of reactive oxygen species (ROS) overwhelm the antioxidant defences in the organism and lead to the oxidative damage of lipids, proteins and nucleic acids. However, these types of ROS are also generated in secondary plants. In particular, one of the free radical attacks is against fatty acids. When the oxidative reaction of ROS is directed against α-linolenic acid (ALA), the predominant polyunsaturated fatty acid (PUFA) in plants, phytoprostanes (PhytoPs) are formed in plant tissues. The PhytoPs levels can increase when plants are subjected to different types of oxidative stress [1]. The most inter- esting aspect of PhytoPs is that they mimic the structure of other eicosanoids such as isoprostanes (IsoPs) and prostanoids (prosta- glandins and thromboxanes), compounds generated by non-enzy- matic free radical attack of arachidonic acid in humans. Eicosa- noids perform a wide range of biological actions in the human body, from pernicious effects (platelet aggregation, vasoconstric- tion) to beneficial effects related to the defense-physiological bal- ance of the body [2]. This fact could lead to the discovery of new properties of phytoprostanes related to different physiological ef- fects and disorders of the human body. Structure and nomenclature As shown in Figure 1, the triene unit is the principal building block for all PhytoP ring systems. The substitutes at the triene unit are the methyl and carboxyl terminus of the fatty acid. The methyl terminal chain at each distinct triene unit can occupy position R 1 or R 2 of the PhytoP, and, thus, two types of regioisomers can be produced per triene unit. Different nomenclature systems have been proposed to identify the structural PhytoPs isomers unambiguously [3]. Initially, Taber and Roberts [4] suggested a nomenclature which was approved by IUPAC and later another nomenclature was proposed by Rokach [5]. This latter nomenclature has the advantage that the biosynthetic Figure 1. Non enzymatic formation of PhytoPs from ALA. DOI 10.1002/lite.201500020 Lipid Technology June 2015, Vol. 27, No. 6 127 © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.lipid-technology.com