{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T05:34:58Z","timestamp":1790832898811,"version":"4.1.0"},"reference-count":101,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2023,5,10]],"date-time":"2023-05-10T00:00:00Z","timestamp":1683676800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceuticals"],"abstract":"<jats:p>About 15% of couples worldwide are affected by infertility, with the male factor responsible for approximately 50% of reproductive failures. Male fertility can be influenced by various factors, including an unhealthy lifestyle and diet, often associated with oxidative stress. These changes are frequently the reason for spermatozoan dysfunction, malformations, and lowered count. However, sometimes even with proper semen parameters, fertilization does not occur, and this is referred to as idiopathic infertility. Of particular importance may be molecules contained in the spermatozoan membrane or seminal plasma, such as polyunsaturated fatty acids, including omega-3 (docosahexaenoic and eicosapentaenoic acids) and omega-6 (arachidonic acid) fatty acids and their derivatives (prostaglandins, leukotrienes, thromboxanes, endocannabinoids, isoprostanes), which are vulnerable to the effects of oxidative stress. In the present review, we discuss the influence of these molecules on human male reproductive health and its possible causes, including disrupted oxidative\u2013antioxidative balance. The review also discusses the potential use of these molecules in the diagnostics and treatment of male infertility, with a particular focus on the innovative approach to isoprostanes as biomarkers for male infertility. Given the high occurrence of idiopathic male infertility, there is a need to explore new solutions for the diagnosis and treatment of this condition.<\/jats:p>","DOI":"10.3390\/ph16050723","type":"journal-article","created":{"date-parts":[[2023,5,10]],"date-time":"2023-05-10T03:32:27Z","timestamp":1683689547000},"page":"723","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["PUFAs and Their Derivatives as Emerging Players in Diagnostics and Treatment of Male Fertility Disorders"],"prefix":"10.3390","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3079-8186","authenticated-orcid":false,"given":"Kamil","family":"Rodak","sequence":"first","affiliation":[{"name":"Department of Laboratory Diagnostics, Division of Laboratory Diagnostics, Faculty of Pharmacy, Wroclaw Medical University, Borowska Street 211A, 50-556 Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2948-4574","authenticated-orcid":false,"given":"Ewa Maria","family":"Kratz","sequence":"additional","affiliation":[{"name":"Department of Laboratory Diagnostics, Division of Laboratory Diagnostics, Faculty of Pharmacy, Wroclaw Medical University, Borowska Street 211A, 50-556 Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,5,10]]},"reference":[{"key":"ref_1","first-page":"31","article-title":"Problem niep\u0142odno\u015bci w\u015br\u00f3d kobiet i m\u0119\u017cczyzn-epidemiologia, czynniki ryzyka i \u015bwiadomo\u015b\u0107 spo\u0142eczna","volume":"2","author":"Koperwas","year":"2017","journal-title":"Asp. Zdrowia Chor."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"810","DOI":"10.1016\/j.fertnstert.2018.08.015","article-title":"Male infertility as a window to health","volume":"110","author":"Choy","year":"2018","journal-title":"Fertil. Steril."},{"key":"ref_3","unstructured":"(2023, January 16). Infertility. Available online: https:\/\/www.who.int\/news-room\/fact-sheets\/detail\/infertility."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"961","DOI":"10.1289\/ehp.00108961","article-title":"The question of declining sperm density revisited: An analysis of 101 studies published 1934\u20131996","volume":"108","author":"Swan","year":"2000","journal-title":"Environ. Health Perspect."},{"key":"ref_5","first-page":"849","article-title":"Infertility","volume":"75","author":"Boyden","year":"2007","journal-title":"Am. Fam. Physician"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1007\/s13596-017-0269-7","article-title":"Classification, causes, diagnosis and treatment of male infertility: A review","volume":"17","author":"Naz","year":"2017","journal-title":"Orient. Pharm. Exp. Med."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1007\/s10508-022-02520-3","article-title":"Does SARS-CoV-2 Affect Human Semen? A Systematic Review and Meta-Analysis","volume":"52","author":"Klepinowski","year":"2023","journal-title":"Arch. Sex. Behav."},{"key":"ref_8","unstructured":"WHO World Health Organization (2021). WHO Laboratory Manual for the Examination and Processing of Human Semen, WHO Press. [6th ed.]."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1038\/nrurol.2014.74","article-title":"Seminal plasma as a diagnostic fluid for male reproductive system disorders","volume":"11","author":"Drabovich","year":"2014","journal-title":"Nat. Rev. Urol."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Cholewski, M., Tomczykowa, M., and Tomczyk, M. (2018). A comprehensive review of chemistry, sources and bioavailability of omega-3 fatty acids. Nutrients, 10.","DOI":"10.3390\/nu10111662"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"S14","DOI":"10.1038\/sj.ejcn.1601478","article-title":"Polyunsaturated fatty acids, inflammation and immunity","volume":"56","author":"Calder","year":"2002","journal-title":"Eur. J. Clin. Nutr."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.plefa.2010.02.028","article-title":"N-3 Polyunsaturated fatty acids-Physiological relevance of dose","volume":"82","author":"Kim","year":"2010","journal-title":"Prostaglandins Leukot. Essent. Fat. Acids"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"101165","DOI":"10.1016\/j.plipres.2022.101165","article-title":"Polyunsaturated fatty acids and fatty acid-derived lipid mediators: Recent advances in the understanding of their biosynthesis, structures, and functions","volume":"86","author":"Dyall","year":"2022","journal-title":"Prog. Lipid Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"511","DOI":"10.1038\/nri3859","article-title":"Eicosanoid storm in infection and inflammation","volume":"15","author":"Dennis","year":"2015","journal-title":"Nat. Rev. Immunol."},{"key":"ref_15","first-page":"38","article-title":"Cell membrane fatty acids and health","volume":"5","author":"Hussein","year":"2013","journal-title":"Int. J. Pharm. Pharm. Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1093\/molehr\/6.3.226","article-title":"Fatty acid composition of spermatozoa and immature germ cells","volume":"6","author":"Lenzi","year":"2000","journal-title":"Mol. Hum. Reprod."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1016\/j.ejphar.2015.03.091","article-title":"Omega-3 fatty acids, lipid rafts, and T cell signaling","volume":"785","author":"Hou","year":"2016","journal-title":"Eur. J. Pharmacol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1016\/j.pnpbp.2006.07.010","article-title":"Omega-3 fatty acids and antioxidants in neurological and psychiatric diseases: An overview","volume":"31","author":"Mazza","year":"2007","journal-title":"Prog. Neuro-Psychopharmacol. Biol. Psychiatry"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1002\/mrd.1052","article-title":"Production of reactive oxygen species by spermatozoa undergoing cooling, freezing, and thawing","volume":"59","author":"Chatterjee","year":"2001","journal-title":"Mol. Reprod. Dev."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1093\/molehr\/4.2.111","article-title":"The fatty acid composition of phospholipids of spermatozoa from infertile patients","volume":"4","author":"Zalata","year":"1998","journal-title":"Mol. Hum. Reprod."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1094","DOI":"10.1111\/andr.12236","article-title":"Fatty acids profiling reveals potential candidate markers of semen quality","volume":"4","author":"Zerbinati","year":"2016","journal-title":"Andrology"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1016\/S0304-4157(00)00018-6","article-title":"Dynamics of the mammalian sperm plasma membrane in the process of fertilization","volume":"1469","author":"Flesch","year":"2000","journal-title":"Biochim. Biophys. Acta-Rev. Biomembr."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1111\/j.1439-0531.2009.01402.x","article-title":"Role of fatty acids in energy provision during oocyte maturation and early embryo development","volume":"44","author":"Sturmey","year":"2009","journal-title":"Reprod. Domest. Anim."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"18","DOI":"10.1186\/s12944-016-0396-z","article-title":"The role of fatty acids on ICSI outcomes: A prospective cohort study","volume":"16","author":"Mirabi","year":"2017","journal-title":"Lipids Health Dis."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1039","DOI":"10.1002\/mrd.22871","article-title":"Reactive oxygen species as mediators of sperm capacitation and pathological damage","volume":"84","author":"Aitken","year":"2017","journal-title":"Mol. Reprod. Dev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"234","DOI":"10.1016\/j.mce.2009.06.009","article-title":"Role and regulation of PI3K in sperm capacitation and the acrosome reaction","volume":"314","author":"Breitbart","year":"2010","journal-title":"Mol. Cell. Endocrinol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1190","DOI":"10.1002\/biot.200800229","article-title":"Polyunsaturated fatty acids inhibit PI3K activity in a yeast-based model system","volume":"4","author":"Couplan","year":"2009","journal-title":"Biotechnol. J."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"793","DOI":"10.1007\/s11745-999-0425-1","article-title":"Fatty acid analysis of blood serum, seminal plasma, and spermatozoa of normozoospermic vs. asthenozoospermic males","volume":"34","author":"Conquer","year":"1999","journal-title":"Lipids"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1111\/j.1439-0272.2006.00735.x","article-title":"Decreased polyunsaturated and increased saturated fatty acid concentration in spermatozoa from asthenozoospermic males as compared with normozoospermic males","volume":"38","author":"Tavilani","year":"2006","journal-title":"Andrologia"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1016\/j.plefa.2006.06.002","article-title":"Sperm fatty acid composition in subfertile men","volume":"75","author":"Aksoy","year":"2006","journal-title":"Prostaglandins Leukot. Essent. Fat. Acids"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"365","DOI":"10.1111\/j.2047-2927.2012.00040.x","article-title":"Spermatozoa and seminal plasma fatty acids as predictors of cryopreservation success","volume":"1","author":"Landeras","year":"2013","journal-title":"Andrology"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"648","DOI":"10.1071\/RD14276","article-title":"Association of decreased spermatozoa omega-3 fatty acid levels and increased oxidative DNA damage with varicocele in infertile men: A case control study","volume":"28","author":"Tang","year":"2016","journal-title":"Reprod. Fertil. Dev."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.plefa.2007.08.003","article-title":"Fatty acid composition of human spermatozoa and seminal plasma levels of oxidative stress biomarkers in subfertile males","volume":"77","author":"Khosrowbeygi","year":"2007","journal-title":"Prostaglandins Leukot. Essent. Fat. Acids"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1111\/j.1439-0272.2009.01013.x","article-title":"Effect of omega-3 polyunsaturated fatty acid supplementation on semen profile and enzymatic anti-oxidant capacity of seminal plasma in infertile men with idiopathic oligoasthenoteratospermia: A double-blind, placebo-controlled, randomised study","volume":"43","author":"Safarinejad","year":"2011","journal-title":"Andrologia"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1080\/01485010151096405","article-title":"Phospholipid composition of human sperm and seminal plasma in relation to sperm fertility","volume":"46","author":"Gulaya","year":"2001","journal-title":"Arch. Androl."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"996","DOI":"10.1111\/obr.12226","article-title":"High-energy diets: A threat for male fertility?","volume":"15","author":"Rato","year":"2014","journal-title":"Obes. Rev."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"467","DOI":"10.1530\/REP-06-00294","article-title":"Essential fatty acid deficiency induces fatty acid desaturase expression in rat epididymis, but not in testis","volume":"133","author":"Tran","year":"2007","journal-title":"Reproduction"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1007\/BF02664764","article-title":"Effect of DHA supplementation on DHA status and sperm motility in asthenozoospermic males","volume":"35","author":"Conquer","year":"2000","journal-title":"Lipids"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"282","DOI":"10.1016\/j.repbio.2018.06.002","article-title":"Effect of dietary supplementation with a highly pure and concentrated docosahexaenoic acid (DHA) supplement on human sperm function","volume":"18","author":"Pinto","year":"2018","journal-title":"Reprod. Biol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"423","DOI":"10.1111\/andr.12348","article-title":"Dietary fatty acids influence sperm quality and function","volume":"5","author":"Ferramosca","year":"2017","journal-title":"Andrology"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"190","DOI":"10.1016\/j.fertnstert.2014.10.010","article-title":"Dietary fatty acid intakes and asthenozoospermia: A case-control study","volume":"103","author":"Eslamian","year":"2015","journal-title":"Fertil. Steril."},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Ayala, A., Mu\u00f1oz, M.F., and Arg\u00fcelles, S. (2014). Lipid peroxidation: Production, metabolism, and signaling mechanisms of malondialdehyde and 4-hydroxy-2-nonenal. Oxid. Med. Cell. Longev., 2014.","DOI":"10.1155\/2014\/360438"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"280","DOI":"10.1111\/andr.297","article-title":"Semen characteristics and malondialdehyde levels in men with different reproductive problems","volume":"3","author":"Collodel","year":"2015","journal-title":"Andrology"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"808","DOI":"10.1007\/s00018-002-8469-8","article-title":"Products of the isoprostane pathway: Unique bioactive compounds and markers of lipid peroxidation","volume":"59","author":"Roberts","year":"2002","journal-title":"Cell. Mol. Life Sci."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"33","DOI":"10.14715\/cmb\/2017.63.10.5","article-title":"Effect of pomegranate (Punica granatum L.) juice on kidney, liver, heart and testis histopathological changes, and the tissues lipid peroxidation and antioxidant status in lead acetate-treated rats","volume":"63","author":"Aksu","year":"2017","journal-title":"Cell. Mol. Biol."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1186\/s12958-019-0468-9","article-title":"Effects of N-acetyl-cysteine supplementation on sperm quality, chromatin integrity and level of oxidative stress in infertile men","volume":"17","author":"Jannatifar","year":"2019","journal-title":"Reprod. Biol. Endocrinol."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1080\/19396368.2016.1246623","article-title":"Dietary supplementation with docosahexaenoic acid (DHA) improves seminal antioxidant status and decreases sperm DNA fragmentation","volume":"62","author":"Domingo","year":"2016","journal-title":"Syst. Biol. Reprod. Med."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"601","DOI":"10.1007\/s11745-001-0763-z","article-title":"Metabolism of very long chain polyunsaturated fatty acids in isolated rat germ cells","volume":"36","author":"Tran","year":"2001","journal-title":"Lipids"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"3640450","DOI":"10.1155\/2020\/3640450","article-title":"Fatty Acid Profile and Metabolism Are Related to Human Sperm Parameters and Are Relevant in Idiopathic Infertility and Varicocele","volume":"2020","author":"Collodel","year":"2020","journal-title":"Mediat. Inflamm."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"354","DOI":"10.1016\/j.envint.2019.05.043","article-title":"Seminal plasma metabolome in relation to semen quality and urinary phthalate metabolites among Chinese adult men","volume":"129","author":"Wang","year":"2019","journal-title":"Environ. Int."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1002\/mrd.22284","article-title":"Metabolomics fingerprinting of the human seminal plasma of asthenozoospermic patients","volume":"81","author":"Gilany","year":"2014","journal-title":"Mol. Reprod. Dev."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"112903","DOI":"10.1016\/j.jpba.2019.112903","article-title":"Metabolic profiling of seminal plasma from teratozoospermia patients","volume":"178","author":"Mehrparvar","year":"2020","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_53","doi-asserted-by":"crossref","unstructured":"Qiao, S., Wu, W., Chen, M., Tang, Q., Xia, Y., Jia, W., and Wang, X. (2017). Seminal plasma metabolomics approach for the diagnosis of unexplained male infertility. PLoS ONE, 12.","DOI":"10.1371\/journal.pone.0181115"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"767","DOI":"10.1016\/j.metabol.2010.07.026","article-title":"Mitochondrial dysfunction during in vitro hepatocyte steatosis is reversed by omega-3 fatty acid-induced up-regulation of mitofusin 2","volume":"60","author":"Zhang","year":"2011","journal-title":"Metabolism."},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Cooray, A., Kim, J.H., Chae, M.R., Lee, S., and Lee, K.P. (2022). Perspectives on Potential Fatty Acid Modulations of Motility Associated Human Sperm Ion Channels. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23073718"},{"key":"ref_56","first-page":"10","article-title":"Curcumin: A Review of Clinical Use and Efficacy","volume":"1","author":"Elgar","year":"2022","journal-title":"Nutr. Med. J."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1091","DOI":"10.3945\/jn.113.190173","article-title":"Processed meat intake is unfavorably and fish intake favorably associated with semen quality indicators among men attending a fertility clinic","volume":"144","author":"Afeiche","year":"2014","journal-title":"J. Nutr."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2680","DOI":"10.1210\/jc.2018-00385","article-title":"Seafood intake, sexual activity, and time to pregnancy","volume":"103","author":"Gaskins","year":"2018","journal-title":"J. Clin. Endocrinol. Metab."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"e1919462","DOI":"10.1001\/jamanetworkopen.2019.19462","article-title":"Associations of Fish Oil Supplement Use with Testicular Function in Young Men","volume":"3","author":"Jensen","year":"2020","journal-title":"JAMA Netw. Open"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1466","DOI":"10.1093\/humrep\/des065","article-title":"Dietary fat and semen quality among men attending a fertility clinic","volume":"27","author":"Attaman","year":"2012","journal-title":"Hum. Reprod."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"794","DOI":"10.1111\/andr.12649","article-title":"The influence of omega-3 fatty acids on semen quality markers: A systematic PRISMA review","volume":"7","author":"Falsig","year":"2019","journal-title":"Andrology"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"3679247","DOI":"10.1155\/2018\/3679247","article-title":"Identification and Quantification of Fatty Acids in T. viridissima, C. biguttulus, and C. brunneus by GC-MS","volume":"2018","author":"Wathne","year":"2018","journal-title":"J. Lipids"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1016\/j.freeradbiomed.2016.12.018","article-title":"DHA-derived oxylipins, neuroprostanes and protectins, differentially and dose-dependently modulate the inflammatory response in human macrophages: Putative mechanisms through PPAR activation","volume":"103","author":"Bosviel","year":"2017","journal-title":"Free Radic. Biol. Med."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1093\/humupd\/dmu004","article-title":"Endocannabinoids as biomarkers of human reproduction","volume":"20","author":"Rapino","year":"2014","journal-title":"Hum. Reprod. Update"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"S237","DOI":"10.1194\/jlr.R800033-JLR200","article-title":"Phospholipase A 2 structure\/function, mechanism, and signaling","volume":"50","author":"Burke","year":"2009","journal-title":"J. Lipid Res."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1530\/jrf.0.0520147","article-title":"Prostaglandin concentrations in the semen of fertile men","volume":"52","author":"Templeton","year":"1978","journal-title":"J. Reprod. Fertil."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"3229","DOI":"10.1016\/S0021-9258(18)48651-6","article-title":"Isolation and identification of prostaglandins from human seminal","volume":"238","author":"Samuelsson","year":"1963","journal-title":"J. Biol. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"622","DOI":"10.1016\/S0015-0282(16)37687-7","article-title":"The relation between fertility and prostaglandin content of seminal fluid in man","volume":"21","author":"Bygdeman","year":"1970","journal-title":"Fertil. Steril."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"868","DOI":"10.1016\/S0015-0282(16)41349-X","article-title":"Seminal prostaglandins in infertile men","volume":"26","author":"Collier","year":"1975","journal-title":"Fertil. Steril."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"1093","DOI":"10.1126\/science.1114338","article-title":"Prostaglandins in human seminal fluid: Two novel compounds","volume":"187","author":"Jonsson","year":"1975","journal-title":"Science"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/S0015-0282(16)47547-3","article-title":"Prostaglandins in semen and their relationship to male fertility: A study of 145 men","volume":"41","author":"Cosentino","year":"1984","journal-title":"Fertil. Steril."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"743","DOI":"10.1016\/S0015-0282(16)47843-X","article-title":"The natural variations in prostaglandin concentration in human seminal fluid and its relation to sperm quality","volume":"41","author":"Bendvold","year":"1984","journal-title":"Fertil. Steril."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1530\/jrf.0.0560195","article-title":"Reduced prostaglandin levels in the semen of men with very high sperm concentrations","volume":"56","author":"Kelly","year":"1979","journal-title":"J. Reprod. Fertil."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/BF03348209","article-title":"Role of seminal prostaglandins in male fertility. I. Relationship of prostaglandin E and 19-OH prostaglandin E with seminal parameters","volume":"3","author":"Isidori","year":"1980","journal-title":"J. Endocrinol. Investig. Off. J. Ital. Soc. Endocrinol."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"434","DOI":"10.1071\/RD14035","article-title":"Low physiological levels of prostaglandins E2 and F2\u03b1 improve human sperm functions","volume":"28","author":"Rios","year":"2016","journal-title":"Reprod. Fertil. Dev."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"3008","DOI":"10.1073\/pnas.95.6.3008","article-title":"A new prostaglandin E receptor mediates calcium influx and acrosome reaction in human spermatozoa","volume":"95","author":"Schaefer","year":"1998","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1095\/biolreprod.112.101956","article-title":"Seminal plasma induces prostaglandin-endoperoxide synthase (PTGS) 2 expression in immortalized human vaginal cells: Involvement of semen prostaglandin E2 in PTGS2 upregulation","volume":"88","author":"Joseph","year":"2013","journal-title":"Biol. Reprod."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"1481","DOI":"10.1136\/gut.2008.175166","article-title":"Human intestinal epithelial cells promote the differentiation of tolerogenic dendritic cells","volume":"58","author":"Iliev","year":"2009","journal-title":"Gut"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1038\/ni1037","article-title":"Regulatory T cells mediate maternal tolerance to the fetus","volume":"5","author":"Aluvihare","year":"2004","journal-title":"Nat. Immunol."},{"key":"ref_80","first-page":"e367","article-title":"Relationship between Human Seminal Prostaglandins on Intrauterine Insemination Pregnancy Outcomes","volume":"3","author":"Holtel","year":"2021","journal-title":"Gynecol. Women\u2019s Health Res."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1016\/0090-6980(83)90156-9","article-title":"Isolation of leukotriene C4 from human seminal fluid","volume":"26","author":"Saad","year":"1983","journal-title":"Prostaglandins"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1016\/0090-6980(92)90020-T","article-title":"The production of arachidonic acid metabolites in rat testis","volume":"44","author":"Reddy","year":"1992","journal-title":"Prostaglandins"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/S0378-4347(00)81426-7","article-title":"Determination of prostaglandins and thromboxane as their pentafluorobenzyl-trimethylsilyl derivatives by electron-capture gas chromatography","volume":"230","author":"Mai","year":"1982","journal-title":"J. Chromatogr. B Biomed. Sci. Appl."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1017\/S0029665113003418","article-title":"PUFA-derived endocannabinoids: An overview","volume":"Volume 72","author":"Cascio","year":"2013","journal-title":"Proceedings of the Nutrition Society"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"4692","DOI":"10.1210\/en.2009-0057","article-title":"Characterization of the endocannabinoid system in human spermatozoa and involvement of transient receptor potential vanilloid 1 receptor in their fertilizing ability","volume":"150","author":"Francavilla","year":"2009","journal-title":"Endocrinology"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"S31","DOI":"10.1016\/j.mce.2008.02.013","article-title":"Endocannabinoids, sperm functions and energy metabolism","volume":"286","author":"Rossato","year":"2008","journal-title":"Mol. Cell. Endocrinol."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"5882","DOI":"10.1210\/en.2010-0484","article-title":"Energetic metabolism and human sperm motility: Impact of CB1 receptor activation","volume":"151","author":"Barbonetti","year":"2010","journal-title":"Endocrinology"},{"key":"ref_88","doi-asserted-by":"crossref","unstructured":"Lewis, S.E.M., Rapino, C., Di Tommaso, M., Pucci, M., Battista, N., Paro, R., Simon, L., Lutton, D., and Maccarrone, M. (2012). Differences in the Endocannabinoid System of Sperm from Fertile and Infertile Men. PLoS ONE, 7.","DOI":"10.1371\/journal.pone.0047704"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"2058","DOI":"10.1093\/humrep\/det232","article-title":"Anandamide modulates human sperm motility: Implications for men with asthenozoospermia and oligoasthenoteratozoospermia","volume":"28","author":"Amoako","year":"2013","journal-title":"Hum. Reprod."},{"key":"ref_90","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 Anal. Technol. Biomed. Life Sci."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/0003-2697(90)90002-Q","article-title":"Noncyclooxygenase oxidative formation of a series of novel prostaglandins: Analytical ramifications for measurement of eicosanoids","volume":"184","author":"Morrow","year":"1990","journal-title":"Anal. Biochem."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"10721","DOI":"10.1073\/pnas.89.22.10721","article-title":"Non-cyclooxygenase-derived prostanoids (F2-isoprostanes) are formed in situ on phospholipids","volume":"89","author":"Morrow","year":"1992","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_93","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_94","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1016\/j.bbalip.2014.10.007","article-title":"The isoprostanes-25 years later","volume":"1851","author":"Milne","year":"2015","journal-title":"Biochim. Biophys. Acta-Mol. Cell Biol. Lipids"},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"e13465","DOI":"10.1111\/and.13465","article-title":"Cytosolic phospholipase A2 and F2 isoprostanes are involved in semen quality and human infertility\u2014A study on leucocytospermia, varicocele and idiopathic infertility","volume":"52","author":"Collodel","year":"2020","journal-title":"Andrologia"},{"key":"ref_96","doi-asserted-by":"crossref","unstructured":"Collodel, G., Moretti, E., Longini, M., Pascarelli, N.A., and Signorini, C. (2018). Increased F2-isoprostane levels in semen and immunolocalization of the 8-iso prostaglandin F2\u03b1 in spermatozoa from infertile patients with varicocele. Oxid. Med. Cell. Longev., 2018.","DOI":"10.1155\/2018\/7508014"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"390","DOI":"10.1080\/19396368.2019.1626934","article-title":"New insights into sperm with total globozoospermia: Increased fatty acid oxidation and centrin1 alteration","volume":"65","author":"Moretti","year":"2019","journal-title":"Syst. Biol. Reprod. Med."},{"key":"ref_98","doi-asserted-by":"crossref","unstructured":"Khosrowbeygi, A., and Zarghami, N. (2007). Levels of oxidative stress biomarkers in seminal plasma and their relationship with seminal parameters. BMC Clin. Pathol., 7.","DOI":"10.1186\/1472-6890-7-6"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"106448","DOI":"10.1016\/j.prostaglandins.2020.106448","article-title":"Relevance of seminal F2-dihomo-IsoPs, F2-IsoPs and F4-NeuroPs in idiopathic infertility and varicocele","volume":"149","author":"Longini","year":"2020","journal-title":"Prostaglandins Other Lipid Mediat."},{"key":"ref_100","doi-asserted-by":"crossref","unstructured":"Moretti, E., Signorini, C., Ferretti, F., Noto, D., and Collodel, G. (2022). A Study to Validate the Relevance of Semen F2-Isoprostanes on Human Male Infertility. Int. J. Environ. Res. Public Health, 19.","DOI":"10.3390\/ijerph19031642"},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"C1619","DOI":"10.1152\/ajpcell.1993.264.6.C1619","article-title":"Evidence for the existence of F2-isoprostane receptors on rat vascular smooth muscle cells","volume":"264","author":"Fukunaga","year":"1993","journal-title":"Am. J. Physiol.-Cell Physiol."}],"container-title":["Pharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8247\/16\/5\/723\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:31:48Z","timestamp":1760124708000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8247\/16\/5\/723"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,5,10]]},"references-count":101,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2023,5]]}},"alternative-id":["ph16050723"],"URL":"https:\/\/doi.org\/10.3390\/ph16050723","relation":{},"ISSN":["1424-8247"],"issn-type":[{"value":"1424-8247","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,5,10]]}}}