{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,28]],"date-time":"2026-01-28T13:44:10Z","timestamp":1769607850829,"version":"3.49.0"},"reference-count":70,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2018,11,16]],"date-time":"2018-11-16T00:00:00Z","timestamp":1542326400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Antioxidants"],"abstract":"<jats:p>Structure-activity relationship (SAR) constitutes a crucial topic to discover new bioactive molecules. This approach initiates with the comparison of a target candidate with a molecule or a collection of molecules and their attributed biological functions to shed some light in the details of one or more SARs and subsequently using that information to outline valuable application of the newly identified compounds. Thus, while the empiric knowledge of medicinal chemistry is critical to these tasks, the results retrieved upon dedicated experimental demonstration retrieved resorting to modern high throughput analytical approaches and techniques allow to overwhelm the constraints adduced so far to the successful accomplishment of such tasks. Therefore, the present work reviews critically the evidences reported to date on the occurrence of phytoprostanes and phytofurans in plant foods, and the information available on their bioavailability and biological activity, shedding some light on the expectation waken up due to their structural similarities with prostanoids and isoprostanes.<\/jats:p>","DOI":"10.3390\/antiox7110165","type":"journal-article","created":{"date-parts":[[2018,11,16]],"date-time":"2018-11-16T11:48:31Z","timestamp":1542368911000},"page":"165","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Structural\/Functional Matches and Divergences of Phytoprostanes and Phytofurans with Bioactive Human Oxylipins"],"prefix":"10.3390","volume":"7","author":[{"given":"Sonia","family":"Medina","sequence":"first","affiliation":[{"name":"CQM\u2014Centro de Qu\u00edmica da Madeira, Universidade da Madeira, Campus da Penteada, 9020-105 Funchal, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7646-0386","authenticated-orcid":false,"given":"\u00c1ngel","family":"Gil-Izquierdo","sequence":"additional","affiliation":[{"name":"Research Group on Quality, Safety and Bioactivity of Plant Foods, Department of Food Science and Technology, CEBAS (CSIC), Campus University Espinardo, 30100 Murcia, Spain"}]},{"given":"Thierry","family":"Durand","sequence":"additional","affiliation":[{"name":"Institut des Biomol\u00e9cules Max Mousseron (IBMM), UMR 5247\u2014CNRS, Faculty of Pharmacy, University of Montpellier\u2014ENSCM, 34093 Montpellier, France"}]},{"given":"Federico","family":"Ferreres","sequence":"additional","affiliation":[{"name":"Research Group on Quality, Safety and Bioactivity of Plant Foods, Department of Food Science and Technology, CEBAS (CSIC), Campus University Espinardo, 30100 Murcia, Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6232-712X","authenticated-orcid":false,"given":"Ra\u00fal","family":"Dom\u00ednguez-Perles","sequence":"additional","affiliation":[{"name":"Research Group on Quality, Safety and Bioactivity of Plant Foods, Department of Food Science and Technology, CEBAS (CSIC), Campus University Espinardo, 30100 Murcia, Spain"}]}],"member":"1968","published-online":{"date-parts":[[2018,11,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1097\/WOX.0b013e3182439613","article-title":"Oxidative stress and antioxidant defense","volume":"5","author":"Birben","year":"2012","journal-title":"World Allergy Organ. J."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1002\/lite.201500020","article-title":"Phytoprostanes","volume":"27","author":"Jacinta","year":"2015","journal-title":"Lipid Technol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"32650","DOI":"10.1074\/jbc.273.49.32650","article-title":"Evidence for the Formation of Dinor Isoprostanes E1from \u03b1-Linolenic Acid in Plants","volume":"273","author":"Parchmann","year":"1998","journal-title":"J. Biol. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"15696","DOI":"10.1039\/C5CC05736A","article-title":"Synthesis and discovery of phytofurans: Metabolites of alpha-linolenic acid peroxidation","volume":"51","author":"Cuyamendous","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"2486","DOI":"10.1002\/ejoc.201700270","article-title":"Total synthesis and in vivo quantitation of phytofurans derived from \u03b1-linolenic acid","volume":"2017","author":"Cuyamendous","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Borrego, E.J., and Kolomiets, M.V. (2016). Synthesis and Functions of Jasmonates in Maize. Plants, 5.","DOI":"10.3390\/plants5040041"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1293","DOI":"10.1104\/pp.124.3.1293","article-title":"Analysis of oxidative stress and wound-inducible dinor isoprostanes F1 (phytoprostanes F1) in plants","volume":"124","author":"Imbusch","year":"2000","journal-title":"Plant Physiol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"720","DOI":"10.1016\/S0891-5849(00)00154-4","article-title":"Formation of isoprostane F2-like compounds (phytoprostanes F1) from \u03b1-linolenic acid in plants","volume":"28","author":"Imbusch","year":"2000","journal-title":"Free Radic. Biol. Med."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.plipres.2017.09.004","article-title":"Isoprostanes, neuroprostanes and phytoprostanes: An overview of 25 years of research in chemistry and biology","volume":"68","author":"Galano","year":"2017","journal-title":"Prog. Lipid Res."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/j.freeradbiomed.2014.04.025","article-title":"Nonenzymatic oxygenated metabolites of alpha-linolenic acid B1- and L1-phytoprostanes protect immature neurons from oxidant injury and promote differentiation of oligodendrocyte progenitors through PPAR-gamma activation","volume":"73","author":"Minghetti","year":"2014","journal-title":"Free Radic. Biol. Med."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"9022","DOI":"10.1021\/acs.jafc.5b03365","article-title":"Dependency of Phytoprostane Fingerprints of Must and Wine on Viticulture and Enological Processes","volume":"63","author":"Marhuenda","year":"2015","journal-title":"J. Agric. Food Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1113","DOI":"10.1007\/s11745-002-1008-x","article-title":"What is the role of alpha-linolenic acid for mammals?","volume":"37","author":"Sinclair","year":"2002","journal-title":"Lipids"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1080\/10715760600939734","article-title":"Biologically active oxidized lipids (phytoprostanes) in the plant diet and parenteral lipid nutrition","volume":"41","author":"Karg","year":"2007","journal-title":"Free Radic. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1890","DOI":"10.3945\/jn.109.108316","article-title":"Flaxseed oil supplementation increases plasma F1-phytoprostanes in healthy men","volume":"139","author":"Barden","year":"2009","journal-title":"J. Nutr."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"95","DOI":"10.3389\/fpls.2011.00095","article-title":"The Alphabet of Galactolipids in Arabidopsis thaliana","volume":"2","author":"Ibrahim","year":"2011","journal-title":"Front. Plant Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"619","DOI":"10.1016\/j.foodres.2018.03.013","article-title":"Sorting out the phytoprostane and phytofuran profile in vegetable oils","volume":"107","author":"Abellan","year":"2018","journal-title":"Food Res. Int."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"212","DOI":"10.1016\/j.foodchem.2015.01.097","article-title":"New UHPLC\u2013QqQ-MS\/MS method for quantitative and qualitative determination of free phytoprostanes in foodstuffs of commercial olive and sunflower oils","volume":"178","author":"Medina","year":"2015","journal-title":"Food Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1585","DOI":"10.1002\/jsfa.7259","article-title":"Effect of the season on the free phytoprostane content in Cornicabra extra virgin olive oil from deficit-irrigated olive trees","volume":"96","author":"Memmi","year":"2016","journal-title":"J. Sci. Food Agric."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"997","DOI":"10.1016\/j.lwt.2015.07.005","article-title":"The phytoprostane content in green table olives is influenced by Spanish-style processing and regulated deficit irrigation","volume":"64","author":"Moriana","year":"2015","journal-title":"LWT-Food Sci. Technol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"6466","DOI":"10.1021\/acs.jafc.5b01904","article-title":"Nonenzymatic alpha-Linolenic Acid Derivatives from the Sea: Macroalgae as Novel Sources of Phytoprostanes","volume":"63","author":"Barbosa","year":"2015","journal-title":"J. Agric. Food Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"452","DOI":"10.1016\/j.foodchem.2018.06.111","article-title":"Isoprostanoids quantitative profiling of marine red and brown macroalgae","volume":"268","author":"Vigor","year":"2018","journal-title":"Food Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.foodchem.2017.02.049","article-title":"Quantification of phytoprostanes\u2013bioactive oxylipins\u2013and phenolic compounds of Passiflora edulis Sims shell using UHPLC-QqQ-MS\/MS and LC-IT-DAD-MS\/MS","volume":"229","author":"Medina","year":"2017","journal-title":"Food Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"801","DOI":"10.12691\/jfnr-5-11-2","article-title":"Valorization strategy of banana passion fruit shell wastes: An innovative source of phytoprostanes and phenolic compounds and their potential use in pharmaceutical and cosmetic industries","volume":"5","author":"Medina","year":"2017","journal-title":"J. Food Nutr. Res."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Medina, S., Collado-Gonz\u00e1lez, J., Ferreres, F., Londo\u00f1o-Londo\u00f1o, J., Jim\u00e9nez-Cartagena, C., Guy, A., Durand, T., Galano, J.M., and Gil-Izquierdo, A. (2018). Potential of Physalis peruviana calyces as a low-cost valuable resource of phytoprostanes and phenolic compounds. J. Sci. Food Agric.","DOI":"10.1002\/jsfa.9413"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1016\/j.foodchem.2016.05.132","article-title":"Impact of packaging atmosphere, storage and processing conditions on the generation of phytoprostanes as quality processing compounds in almond kernels","volume":"211","author":"Aguayo","year":"2016","journal-title":"Food Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"51233","DOI":"10.1039\/C5RA07803B","article-title":"Phytoprostanes in almonds: Identification, quantification, and impact of cultivar and type of cultivation","volume":"5","author":"Aguayo","year":"2015","journal-title":"RSC Adv."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1080\/10715762.2017.1288909","article-title":"Impact of processing conditions on the phytoprostanes profile of three types of nut kernels","volume":"51","author":"Aguayo","year":"2017","journal-title":"Free Radic. Res."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"8938","DOI":"10.1021\/acs.jafc.7b03482","article-title":"Comparative Study of the Phytoprostane and Phytofuran Content of indica and japonica Rice (Oryza sativa L.) Flours","volume":"65","author":"Pinciroli","year":"2017","journal-title":"J. Agric. Food Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1046\/j.1365-313X.2003.01730.x","article-title":"Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants","volume":"34","author":"Thoma","year":"2003","journal-title":"Plant J. Cell Mol. Biol."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"8296","DOI":"10.1021\/acs.jafc.6b03011","article-title":"Thermal Stress in Melon Plants: Phytoprostanes and Phytofurans as Oxidative Stress Biomarkers and the Effect of Antioxidant Supplementation","volume":"64","author":"Yonny","year":"2016","journal-title":"J. Agric. Food Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1016\/j.chemphyslip.2003.10.002","article-title":"The isoprostanoid pathway in plants","volume":"128","author":"Thoma","year":"2004","journal-title":"Chem. Phys. Lipids"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"328","DOI":"10.1104\/pp.104.051714","article-title":"B(1)-Phytoprostanes Trigger Plant Defense and Detoxification Responses","volume":"137","author":"Loeffler","year":"2005","journal-title":"Plant Physiol."},{"key":"ref_33","first-page":"1716","article-title":"General approach to prostanes b1 by intermolecular pauson\u2013khand reaction: Syntheses of methyl esters of prostaglandin b1 and phytoprostanes 16-b1-phytop and 9-l1-phytop","volume":"2013","author":"Verdaguer","year":"2009","journal-title":"Eur. J. Org. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1016\/j.jaci.2007.03.017","article-title":"Immunomodulatory effects of aqueous birch pollen extracts and phytoprostanes on primary immune responses in vivo","volume":"120","author":"Gutermuth","year":"2007","journal-title":"J. Allergy Clin. Immunol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3784","DOI":"10.1021\/acs.jafc.5b00805","article-title":"Water deficit during pit hardening enhances phytoprostanes content, a plant biomarker of oxidative stress, in extra virgin olive oil","volume":"63","author":"Memmi","year":"2015","journal-title":"J. Agric. Food Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"372","DOI":"10.1016\/S1369-5266(03)00045-1","article-title":"Jasmonates and related oxylipins in plant responses to pathogenesis and herbivory","volume":"6","author":"Farmer","year":"2003","journal-title":"Curr. Opin. Plant Biol."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/j.jchromb.2014.04.042","article-title":"Non-enzymatic lipid oxidation products in biological systems: Assessment of the metabolites from polyunsaturated fatty acids","volume":"964","author":"Vigor","year":"2014","journal-title":"J. Chromatogr. B"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1016\/j.biochi.2016.08.002","article-title":"The novelty of phytofurans, isofurans, dihomo-isofurans and neurofurans: Discovery, synthesis and potential application","volume":"130","author":"Cuyamendous","year":"2016","journal-title":"Biochimie"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2498","DOI":"10.1021\/jo035638i","article-title":"Total synthesis of the eight diastereomers of the syn-anti-syn phytoprostanes F1 types I and II","volume":"69","author":"Guy","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"989","DOI":"10.1021\/jo048179+","article-title":"A flexible synthesis of the phytoprostanes B1 type I and II","volume":"70","author":"Guy","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1002\/cbic.200400259","article-title":"Total synthesis and biological activity of 13,14-dehydro-12-oxo-phytodienoic acids (deoxy-J1-phytoprostanes)","volume":"6","author":"Iqbal","year":"2005","journal-title":"ChemBioChem"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"15533","DOI":"10.1074\/jbc.R700047200","article-title":"Human biochemistry of the isoprostane pathway","volume":"283","author":"Milne","year":"2008","journal-title":"J. Biol. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"4","DOI":"10.1016\/j.prostaglandins.2017.05.002","article-title":"Highly unsaturated fatty acids (HUFA) mediate and monitor food\u2019s impact on health","volume":"133","author":"Lands","year":"2017","journal-title":"Prostaglandins Other Lipid Mediat."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1791","DOI":"10.1096\/fj.04-2330rev","article-title":"Isoprostanes: Markers and mediators of oxidative stress","volume":"18","author":"Montuschi","year":"2004","journal-title":"FASEB J."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"6653","DOI":"10.4049\/jimmunol.0802613","article-title":"Pollen-Derived E1-Phytoprostanes Signal via PPAR-\u03b3 and NF-\u03baB-Dependent Mechanisms","volume":"182","author":"Gilles","year":"2009","journal-title":"J. Immunol."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"627","DOI":"10.1084\/jem.20041065","article-title":"Pollen-associated phytoprostanes inhibit dendritic cell interleukin-12 production and augment T helper type 2 cell polarization","volume":"201","author":"Mariani","year":"2005","journal-title":"J. Exp. Med."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1002\/med.1006","article-title":"Cyclopentenone prostaglandins: New insights on biological activities and cellular targets","volume":"21","author":"Straus","year":"2001","journal-title":"Med. Res. Rev."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"6129","DOI":"10.1021\/bi00524a033","article-title":"Albumin-lipid interactions: Prostaglandin stability as a probe for characterizing binding sites on vertebrate albumins","volume":"20","author":"Fitzpatrick","year":"1981","journal-title":"Biochemistry"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"768","DOI":"10.1105\/tpc.107.054809","article-title":"General detoxification and stress responses are mediated by oxidized lipids through TGA transcription factors in Arabidopsis","volume":"20","author":"Mueller","year":"2008","journal-title":"Plant Cell"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"7623","DOI":"10.4049\/jimmunol.178.12.7623","article-title":"Immunomodulatory mediators from pollen enhance the migratory capacity of dendritic cells and license them for Th2 attraction","volume":"178","author":"Mariani","year":"2007","journal-title":"J. Immunol."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"35562","DOI":"10.1074\/jbc.M504785200","article-title":"Cyclopentenone isoprostanes inhibit the inflammatory response in macrophages","volume":"280","author":"Musiek","year":"2005","journal-title":"J. Biol. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"7367","DOI":"10.1073\/pnas.112212599","article-title":"15-Deoxy-\u0394(12,14)-prostaglandin J(2): The endogenous electrophile that induces neuronal apoptosis","volume":"99","author":"Kondo","year":"2002","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1099","DOI":"10.1096\/fj.02-0485fje","article-title":"Suppression of endothelial adhesion molecule up-regulation with cyclopentenone prostaglandins is dissociated from IkappaB-alpha kinase inhibition and cell death induction","volume":"17","author":"Zernecke","year":"2003","journal-title":"FASEB J."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"S140","DOI":"10.1016\/S0959-8049(16)61494-6","article-title":"627-Oxidized products of \u03b1-linolenic acid negatively affect cell survival and motility of breast cancer cells","volume":"61","author":"Oger","year":"2016","journal-title":"Eur. J. Cancer"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"5741","DOI":"10.1016\/S0040-4039(03)01297-8","article-title":"Conjugate addition\u2013Peterson olefination reactions: Expedient routes to cross conjugated dienones","volume":"44","author":"Iqbal","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"803","DOI":"10.1016\/0092-8674(95)90193-0","article-title":"15-Deoxy-delta 12, 14-prostaglandin J2 is a ligand for the adipocyte determination factor PPAR gamma","volume":"83","author":"Forman","year":"1995","journal-title":"Cell"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"813","DOI":"10.1016\/0092-8674(95)90194-9","article-title":"A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor gamma and promotes adipocyte differentiation","volume":"83","author":"Kliewer","year":"1995","journal-title":"Cell"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1152\/physrev.1999.79.4.1193","article-title":"Prostanoid receptors: Structures, properties, and functions","volume":"79","author":"Narumiya","year":"1999","journal-title":"Physiol. Rev."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1038\/34184","article-title":"PPAR-gamma agonists inhibit production of monocyte inflammatory cytokines","volume":"391","author":"Jiang","year":"1998","journal-title":"Nature"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1038\/34178","article-title":"The peroxisome proliferator-activated receptor-gamma is a negative regulator of macrophage activation","volume":"391","author":"Ricote","year":"1998","journal-title":"Nature"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"986","DOI":"10.1161\/ATVBAHA.110.207449","article-title":"Prostaglandins and inflammation","volume":"31","author":"Ricciotti","year":"2011","journal-title":"Arterioscler. Thromb. Vasc. Biol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1126\/science.8418493","article-title":"Organic synthesis of prostaglandins: Advancing biology","volume":"259","author":"Noyori","year":"1993","journal-title":"Science"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"3760","DOI":"10.1021\/bi00467a023","article-title":"Formation of thiol conjugates of 9-deoxy-D9 D12(E)-prostaglandin D2 and D12(E)-prostaglandin D2","volume":"29","author":"Atsmon","year":"1990","journal-title":"Biochemistry"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1383","DOI":"10.1016\/S0006-2952(99)00048-9","article-title":"Interactions of prostaglandin A2 with the glutathione-mediated biotransformation system","volume":"57","author":"Cnubben","year":"1999","journal-title":"Biochem. Pharmacol."},{"key":"ref_65","first-page":"189","article-title":"Prostaglandin J2-anti-tumour and anti-viral activities and the mechanisms involved","volume":"3","author":"Fukushima","year":"1990","journal-title":"Eicosanoids"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/S0167-4781(97)00214-5","article-title":"Effects of cyclopentenone prostaglandins and related compounds on insulin-like growth factor-I and Waf1 gene expression","volume":"1397","author":"Bui","year":"1998","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"645","DOI":"10.1093\/carcin\/bgp012","article-title":"15-Deoxy-Delta12,14-prostaglandin J2 upregulates the expression of heme oxygenase-1 and subsequently matrix metalloproteinase-1 in human breast cancer cells: Possible roles of iron and ROS","volume":"30","author":"Kim","year":"2009","journal-title":"Carcinogenesis"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"32192","DOI":"10.1074\/jbc.271.50.32192","article-title":"2-Cyclopenten-1-one, a new inducer of heat shock protein 70 with antiviral activity","volume":"271","author":"Rossi","year":"1996","journal-title":"J. Biol. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"4844","DOI":"10.1073\/pnas.97.9.4844","article-title":"15-Deoxy-\u0394(12,14)-prostaglandin J(2) inhibits multiple steps in the NF-\u03baB signaling pathway","volume":"97","author":"Straus","year":"2000","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1038\/47520","article-title":"Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IkappaB kinase","volume":"403","author":"Rossi","year":"2000","journal-title":"Nature"}],"container-title":["Antioxidants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2076-3921\/7\/11\/165\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:30:14Z","timestamp":1760196614000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2076-3921\/7\/11\/165"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,11,16]]},"references-count":70,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2018,11]]}},"alternative-id":["antiox7110165"],"URL":"https:\/\/doi.org\/10.3390\/antiox7110165","relation":{},"ISSN":["2076-3921"],"issn-type":[{"value":"2076-3921","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,11,16]]}}}