{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,7]],"date-time":"2026-09-07T15:56:32Z","timestamp":1788796592027,"version":"build-2803163510"},"reference-count":62,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2017,2,1]],"date-time":"2017-02-01T00:00:00Z","timestamp":1485907200000},"content-version":"am","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2017,2,1]],"date-time":"2017-02-01T00:00:00Z","timestamp":1485907200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002241","name":"Japan Science and Technology Agency","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100002241","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["febs.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["FEBS Open Bio"],"published-print":{"date-parts":[[2017,3]]},"abstract":"<jats:sec>\n                    <jats:label\/>\n                    <jats:p>\n                      Specialized arthropods and more than 2500 plant species biosynthesize hydroxynitriles and release hydrogen cyanide as a defensive mechanism. The millipede\n                      <jats:italic>Chamberlinius hualienensis<\/jats:italic>\n                      accumulates (\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010mandelonitrile as a cyanide precursor. Although biosynthesis of hydroxynitriles in cyanogenic plants and in an insect are extensively studied, (\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010mandelonitrile biosynthesis in cyanogenic millipedes has remained unclear. In this study, we identified the biosynthetic precursors of (\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010mandelonitrile and an enzyme involved in (\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010mandelonitrile biosynthesis. Using deuterium\u2010labelled compounds, we revealed that (\n                      <jats:italic>E<\/jats:italic>\n                      \/\n                      <jats:italic>Z<\/jats:italic>\n                      )\u2010phenylacetaldoxime and phenylacetonitrile are the biosynthetic precursors of (\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010mandelonitrile in the millipede as well as other cyanogenic organisms. To identify the enzymes involved in (\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010mandelonitrile biosynthesis, 50 c\n                      <jats:styled-content style=\"fixed-case\">DNA<\/jats:styled-content>\n                      s encoding cytochrome P450s were cloned and coexpressed with yeast cytochrome P450 reductase in yeast, as cytochrome P450s are involved in the biosynthesis of hydroxynitriles in other cyanogenic organisms. Among the 50 cytochrome P450s from the millipede,\n                      <jats:styled-content style=\"fixed-case\">CYP<\/jats:styled-content>\n                      3201B1 produced (\n                      <jats:italic>R<\/jats:italic>\n                      )\u2010mandelonitrile from phenylacetonitrile but not from (\n                      <jats:italic>E<\/jats:italic>\n                      \/\n                      <jats:italic>Z<\/jats:italic>\n                      )\u2010phenylacetaldoxime, whereas plant and insect cytochrome P450s catalysed the dehydration of aldoximes and hydroxylation of nitriles.\n                      <jats:styled-content style=\"fixed-case\">CYP<\/jats:styled-content>\n                      3201B1 is not phylogenetically related to cytochrome P450s from other cyanogenic organisms, indicating that hydroxynitrile biosynthetic cytochrome P450s have independently evolved in distant species. Our study will shed light on the evolution of cyanogenesis among plants, insects and millipedes.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Database<\/jats:title>\n                    <jats:p>\n                      Nucleotide sequence data are available in the\n                      <jats:styled-content style=\"fixed-case\">DDBJ<\/jats:styled-content>\n                      \/\n                      <jats:styled-content style=\"fixed-case\">EMBL<\/jats:styled-content>\n                      \/GenBank databases under the accession numbers\n                      <jats:ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" ext-link-type=\"DDBJ\/EMBL\/GenBank\" xlink:href=\"LC125356\">LC125356<\/jats:ext-link>\n                      \u2013\n                      <jats:ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" ext-link-type=\"DDBJ\/EMBL\/GenBank\" xlink:href=\"LC125405\">LC125405<\/jats:ext-link>\n                      .\n                    <\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/2211-5463.12170","type":"journal-article","created":{"date-parts":[[2016,12,7]],"date-time":"2016-12-07T09:33:01Z","timestamp":1481103181000},"page":"335-347","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":31,"title":["A novel cytochrome P450,\n                    <scp>CYP<\/scp>\n                    3201B1, is involved in (\n                    <i>R<\/i>\n                    )\u2010mandelonitrile biosynthesis in a cyanogenic millipede"],"prefix":"10.1002","volume":"7","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7533-430X","authenticated-orcid":false,"given":"Takuya","family":"Yamaguchi","sequence":"first","affiliation":[{"name":"Biotechnology Research Center and Department of Biotechnology Toyama Prefectural University Imizu Japan"},{"name":"JST ERATO Asano Active 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