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Using recent paleontological findings, we discuss the deep homology of the zygomatic or jugal bone in stem gnathostomes (placoderms) and examine its homology and modifications in crown gnathostomes (acanthodians, chondrichthyans and osteichthyans). The discovery of the placoderm <jats:italic>Entelognathus<\/jats:italic> from the Silurian of China (\u223c423 million years ago) established that the large dermal plates in placoderms and osteichthyans are homologous. In <jats:italic>Entelognathus<\/jats:italic>, the jugal was joined by a new set of bones (premaxilla, maxilla, and lachrymal), marking the first appearance of the typical vertebrate face found in tetrapods including humans. In non\u2010<jats:italic>Entelognathus<\/jats:italic> placoderms, the jugal (homologized with the suborbital plate) occupied most of the cheek region and covered the palatoquadrate laterally. In antiarch placoderms (the most basal jawed vertebrates), the jugal (represented by the ventrally positioned mental plate) functioned as part of the upper jaw. In osteichthyans, the preopercular arose as a novel bone and separated the jugal from the opercular in piscine osteichthyans. A single bone in basal osteichthyans, the preopercular may have divided into two or three elements (the preopercular, the squamosal and\/or the quadratojugal) in several later osteichthyan groups. Subsequent modifications of the jugal in the fish\u2010tetrapod transition (its enlargement leading to its contact with the quadratojugal and the separation of the squamosal from the maxilla) brought the vertebrate face to the typical model we see in living tetrapods. Anat Rec, 300:16\u201329, 2017. \u00a9 2016 Wiley Periodicals, Inc.<\/jats:p>","DOI":"10.1002\/ar.23512","type":"journal-article","created":{"date-parts":[[2016,12,21]],"date-time":"2016-12-21T02:15:49Z","timestamp":1482286549000},"page":"16-29","source":"Crossref","is-referenced-by-count":8,"title":["<scp>T<\/scp>he <scp>E<\/scp>volution of the <scp>Z<\/scp>ygomatic <scp>B<\/scp>one <scp>F<\/scp>rom <scp>A<\/scp>gnatha to <scp>T<\/scp>etrapoda"],"prefix":"10.1002","volume":"300","author":[{"given":"Zhikun","family":"Gai","sequence":"first","affiliation":[{"name":"Key Laboratory of Vertebrate Evolution and Human Origins of Chinese Academy of Sciences Institute of Vertebrate Paleontology and Paleoanthropology Chinese Academy of Sciences Beijing 100044 China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xiaobo","family":"Yu","sequence":"additional","affiliation":[{"name":"Department of Biological Sciences Kean University Union New Jersey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Min","family":"Zhu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Vertebrate Evolution and Human Origins of Chinese Academy of Sciences Institute of Vertebrate Paleontology and Paleoanthropology Chinese Academy of Sciences Beijing 100044 China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2016,12,21]]},"reference":[{"doi-asserted-by":"publisher","key":"e_1_2_6_2_1","DOI":"10.1111\/j.1096-3642.1991.tb00905.x"},{"doi-asserted-by":"publisher","key":"e_1_2_6_3_1","DOI":"10.1017\/S0263593300001309"},{"key":"e_1_2_6_4_1","first-page":"165","volume-title":"Devonian fishes and plants of Miguasha, Quebec, Canada","author":"Arratia G","year":"1996"},{"key":"e_1_2_6_5_1","first-page":"153","article-title":"The cranial cartilages of teleosts and their classification","volume":"169","author":"Benjamin M.","year":"1990","journal-title":"J 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