{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T02:07:36Z","timestamp":1790042856272,"version":"4.0.1"},"reference-count":31,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2022,12,29]],"date-time":"2022-12-29T00:00:00Z","timestamp":1672272000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["20K05840"],"award-info":[{"award-number":["20K05840"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["The Plant Journal"],"published-print":{"date-parts":[[2023,2]]},"abstract":"<jats:title>SUMMARY<\/jats:title><jats:p>The phenylpropene volatiles dillapiole and apiole impart one of the characteristic aromas of dill (<jats:italic>Anethum graveolens<\/jats:italic>) weeds. However, very few studies have been conducted to investigate the chemical composition of volatile compounds from different developmental stages and plant parts of <jats:italic>A. graveolens<\/jats:italic>. In this study, we examined the distribution of volatile phenylpropenes, including dillapiole, in dill plants at various developmental stages. We observed that young dill seedlings accumulate high levels of dillapiole and apiole, whereas a negligible proportion was found in the flowering plants and dry seeds. Based on transcriptomics and co\u2010expression approaches with phenylpropene biosynthesis genes, we identified dill cDNA encoding <jats:italic>S<\/jats:italic>\u2010adenosyl\u2010L\u2010methionine\u2010dependent <jats:italic>O<\/jats:italic>\u2010methyltransferase 1 (AgOMT1), an enzyme that can convert 6\u2010 and 2\u2010hydroxymyristicin to dillapiole and apiole, respectively, via the methylation of the <jats:italic>ortho<\/jats:italic>\u2010hydroxy group. The AgOMT1 protein shows an apparent <jats:italic>K<\/jats:italic><jats:sub>m<\/jats:sub> value of 3.5\u00a0\u03bc<jats:sc>m<\/jats:sc> for 6\u2010hydroxymyristicin and is 75% identical to the anise (<jats:italic>Pimpinella anisum<\/jats:italic>) <jats:italic>O<\/jats:italic>\u2010methyltransferase (PaAIMT1) that can convert isoeugenol to methylisoeugenol via methylation of the hydroxy group at the <jats:italic>para<\/jats:italic>\u2010position of the benzene ring. AgOMT1 showed a preference for 6\u2010hydroxymyristicin, whereas PaAIMT1 displayed a large preference for isoeugenol. <jats:italic>In vitro<\/jats:italic> mutagenesis experiments demonstrated that substituting only a few residues can substantially affect the substrate specificity of these enzymes. Other plants belonging to the Apiaceae family contained homologous <jats:italic>O<\/jats:italic>\u2010methyltransferase (OMT) proteins highly similar to AgOMT1, converting 6\u2010hydroxymyristicin to dillapiole. Our results indicate that apiaceous phenylpropene OMTs with <jats:italic>ortho<\/jats:italic>\u2010methylating activity evolved independently of phenylpropene OMTs of other plants and the enzymatic function of AgOMT1 and PaAIMT1 diverged recently.<\/jats:p>","DOI":"10.1111\/tpj.16068","type":"journal-article","created":{"date-parts":[[2022,12,19]],"date-time":"2022-12-19T15:55:00Z","timestamp":1671465300000},"page":"562-575","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Biosynthesis of dillapiole\/apiole in dill (<i>Anethum graveolens<\/i>): characterization of regioselective phenylpropene <i>O<\/i>\u2010methyltransferase"],"prefix":"10.1111","volume":"113","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0786-3242","authenticated-orcid":false,"given":"Takao","family":"Koeduka","sequence":"first","affiliation":[{"name":"Graduate School of Sciences and Technology for Innovation Yamaguchi University  Yamaguchi 753\u20108515 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bunta","family":"Watanabe","sequence":"additional","affiliation":[{"name":"Chemistry Laboratory The Jikei University School of Medicine  8\u20103\u20101 Kokuryo, Chofu, Tokyo 182\u20108570 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Konomi","family":"Shirahama","sequence":"additional","affiliation":[{"name":"Graduate School of Sciences and Technology for Innovation Yamaguchi University  Yamaguchi 753\u20108515 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masaru","family":"Nakayasu","sequence":"additional","affiliation":[{"name":"Research Institute for Sustainable Humanosphere (RISH) Kyoto University  Uji, Kyoto 611\u20100011 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shiro","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Faculty of Applied Biological Sciences Gifu University  1\u20101 Yanagido, Gifu City, Gifu 501\u20101193 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takumi","family":"Furuta","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry Kyoto Pharmaceutical University  Yamashina\u2010ku, Kyoto 607\u20108414 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hideyuki","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Department of Research and Development, Hirata Corporation  111 Hitotsugi, Ueki, Kita, Kumamoto\u2010shi, Kumamoto 861\u20100198 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenji","family":"Matsui","sequence":"additional","affiliation":[{"name":"Graduate School of Sciences and Technology for Innovation Yamaguchi University  Yamaguchi 753\u20108515 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomoyuki","family":"Kosaka","sequence":"additional","affiliation":[{"name":"Graduate School of Sciences and Technology for Innovation Yamaguchi University  Yamaguchi 753\u20108515 Japan"},{"name":"Research Center for Thermotolerant Microbial Resources (RCTMR) Yamaguchi University  Yamaguchi 753\u20108515 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shin\u2010ichi","family":"Ozaki","sequence":"additional","affiliation":[{"name":"Graduate School of Sciences and Technology for Innovation Yamaguchi University  Yamaguchi 753\u20108515 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