{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T19:43:32Z","timestamp":1792784612857,"version":"4.5.0"},"reference-count":40,"publisher":"American Chemical Society (ACS)","issue":"9","license":[{"start":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T00:00:00Z","timestamp":1788825600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T00:00:00Z","timestamp":1788825600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T00:00:00Z","timestamp":1788825600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"name":"Core-Facility at Okayama University","id":[{"id":"https:\/\/ror.org\/02pc6pc55","id-type":"ROR","asserted-by":"crossref"}]},{"DOI":"10.13039\/100007684","name":"Asahi Glass Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007684","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Grant-in-Aid for Scientific Research (C) from the Japan Society for the Promotion of Science","award":["22K05683"],"award-info":[{"award-number":["22K05683"]}],"id":[{"id":"https:\/\/ror.org\/00hhkn466","id-type":"ROR","asserted-by":"crossref"}]},{"name":"JSPS KAKENHI","award":["24K08958"],"award-info":[{"award-number":["24K08958"]}]},{"name":"JSPS KAKENHI","award":["26K00237"],"award-info":[{"award-number":["26K00237"]}]},{"name":"JSPS KAKENHI","award":["26K08834"],"award-info":[{"award-number":["26K08834"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Arthropods use chemical defenses against predators by releasing toxic or repellent compounds from specialized exocrine glands. Oribatulid mites (Oribatida: Oribatulidae) contain mandelonitrile hexanoate (MNH); when they are subjected to physical stimuli, MNH decomposes to release hydrogen cyanide (HCN), suggesting that cyanogenesis is an effective defense strategy in these mites. However, the underlying process remains unclear. Here, we investigated the defensive secretions of the oribatid mites, Phauloppia adjecta and Oribatula sakamorii, and identified MNH and mandelonitrile octanoate (MNO), along with the sesquiterpenes \u03b2-selinene and calarene. Chiral gas chromatography analysis determined the absolute configurations of MNH and MNO as the (R)-isomers, consistent with the configuration of mandelonitrile\ue5f8a known defensive compound in polydesmid millipedes. (R)-MNO did not undergo spontaneous hydrolysis in water at pH 3\u22128, suggesting that a mite-derived enzyme is required for HCN production. In vitro experiments showed that a crude mite enzyme extract incubated with (R)-MNO generated over 200 nmol of HCN, whereas negligible production occurred in the controls. These findings support an enzyme-dependent cyanogenic defense mechanism wherein mandelonitrile esters stored in the oil glands release HCN upon enzyme interaction during disturbance, potentially protecting conspecifics from predation.<\/jats:p>","DOI":"10.1021\/acs.jnatprod.6c00671","type":"journal-article","created":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T16:02:07Z","timestamp":1788883327000},"page":"2527-2535","source":"Crossref","is-referenced-by-count":0,"title":["Enzymatic Hydrogen Cyanide Release from Mandelonitrile Esters in Oribatid Mites"],"prefix":"10.1021","volume":"89","author":[{"given":"Daisuke","family":"Moriyama","sequence":"first","affiliation":[{"name":"Kyoto University of Advanced Science , , 1-1 Nanjo, Sogabe , ,","place":["Kameoka, Japan, 621-8555"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chihiro","family":"Takahara","sequence":"additional","affiliation":[{"name":"Kyoto University of Advanced Science , , 1-1 Nanjo, Sogabe , ,","place":["Kameoka, Japan, 621-8555"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8672-4362","authenticated-orcid":true,"given":"Satoshi","family":"Shimano","sequence":"additional","affiliation":[{"name":"Hosei University , , 2-17-1 Fujimi , , ,","place":["Chiyoda-ku, Tokyo, Japan, 102-8160"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8658-6887","authenticated-orcid":true,"given":"Nobuhiro","family":"Shimizu","sequence":"additional","affiliation":[{"name":"Kyoto University of Advanced Science , , 1-1 Nanjo, Sogabe , ,","place":["Kameoka, Japan, 621-8555"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,8]]},"reference":[{"key":"2026100909072059900_cit1","volume-title":"Secret Weapons: Defenses of Insects, Spiders, Scorpions, and Other Many-Legged Creatures","author":"Eisner","year":"2005"},{"issue":"1","key":"2026100909072059900_cit2","doi-asserted-by":"publisher","first-page":"211","DOI":"10.1146\/annurev.en.33.010188.001235","article-title":"Chemical ecology of the Heteroptera","volume":"33","author":"Aldrich","year":"1988","journal-title":"Annu. 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(Tokyo)"},{"key":"2026100909072059900_cit35","first-page":"7","article-title":"Form and function","volume-title":"Oribatid Mites: Biodiversity, Taxonomy and Ecology","author":"Behan-Pelletier","year":"2023"},{"key":"2026100909072059900_cit36","first-page":"345","article-title":"Oribatida","volume-title":"Pictorial Keys to Soil Animals of Japan","author":"Ohkubo","year":"2015","edition":"2"},{"issue":"2","key":"2026100909072059900_cit37","doi-asserted-by":"publisher","first-page":"530","DOI":"10.24349\/pocc-d7lm","article-title":"A new species of the genus Achipteria Berlese, 1885 (Acariformes, Oribatida, Achipteriidae) from the Kingdom of Bhutan","volume":"66","author":"Oshima","year":"2026","journal-title":"Acarologia"},{"key":"2026100909072059900_cit38","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1017\/CBO9780511542664.004","article-title":"Chemical Ecology of Astigmatid Mites","volume-title":"Advances in Insect Chemical Ecology","author":"Kuwahara","year":"2004"},{"issue":"7","key":"2026100909072059900_cit39","doi-asserted-by":"publisher","first-page":"1681","DOI":"10.1023\/A:1024235100289","article-title":"\u03b1-Acaridial a female sex pheromone from an alarm pheromone emitting mite Rhizoglyphus robini","volume":"29","author":"Mizoguchi","year":"2003","journal-title":"J. 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Biochem."}],"container-title":["Journal of Natural Products"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jnatprod.6c00671","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jnprdf\/article-pdf\/89\/9\/2527\/68683158\/np6c00671.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jnprdf\/article-pdf\/89\/9\/2527\/68683158\/np6c00671.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T13:19:06Z","timestamp":1791551946000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jnprdf\/article\/89\/9\/2527\/5426455\/Enzymatic-Hydrogen-Cyanide-Release-from"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,8]]},"references-count":40,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2026,9,8]]},"published-print":{"date-parts":[[2026,9,25]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jnatprod.6c00671","relation":{},"ISSN":["0163-3864","1520-6025"],"issn-type":[{"value":"0163-3864","type":"print"},{"value":"1520-6025","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,8]]}}}