{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,6]],"date-time":"2026-06-06T08:28:26Z","timestamp":1780734506199,"version":"3.54.1"},"reference-count":46,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2020,10,11]],"date-time":"2020-10-11T00:00:00Z","timestamp":1602374400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["18K05571"],"award-info":[{"award-number":["18K05571"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["19K05857"],"award-info":[{"award-number":["19K05857"]}],"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":[[2020,11]]},"abstract":"<jats:title>Summary<\/jats:title><jats:p><jats:italic>Sesamum<\/jats:italic> spp. (sesame) are known to accumulate a variety of lignans in a lineage\u2010specific manner. In cultivated sesame (<jats:italic>Sesamum indicum<\/jats:italic>), (+)\u2010sesamin, (+)\u2010sesamolin and (+)\u2010sesaminol triglucoside are the three major lignans found richly in the seeds. A recent study demonstrated that SiCYP92B14 is a pivotal enzyme that allocates the substrate (+)\u2010sesamin to two products, (+)\u2010sesamolin and (+)\u2010sesaminol, through multiple reaction schemes including oxidative rearrangement of \u03b1\u2010oxy\u2010substituted aryl groups (ORA). In contrast, it remains unclear whether (+)\u2010sesamin in wild sesame undergoes oxidation reactions as in <jats:italic>S. indicum<\/jats:italic> and how, if at all, the ratio of the co\u2010products is tailored at the molecular level. Here, we functionally characterised SrCYP92B14 as a SiCYP92B14 orthologue from a wild sesame, <jats:italic>Sesamum radiatum<\/jats:italic>, in which we revealed accumulation of the (+)\u2010sesaminol derivatives (+)\u2010sesangolin and its novel structural isomer (+)\u20107\u00b4\u2010episesantalin. Intriguingly, SrCYP92B14 predominantly produced (+)\u2010sesaminol either through ORA or direct oxidation on the aromatic ring, while a relatively low but detectable level of (+)\u2010sesamolin was produced. Amino acid substitution analysis suggested that residues in the putative distal helix and the neighbouring heme propionate of CYP92B14 affect the ratios of its co\u2010products. These data collectively show that the bimodal oxidation mechanism of (+)\u2010sesamin might be widespread across <jats:italic>Sesamum<\/jats:italic> spp., and that CYP92B14 is likely to be a key enzyme in shaping the ratio of (+)\u2010sesaminol\u2010 and (+)\u2010sesamolin\u2010derived lignans from the biochemical and evolutionary perspectives.<\/jats:p>","DOI":"10.1111\/tpj.14989","type":"journal-article","created":{"date-parts":[[2020,9,21]],"date-time":"2020-09-21T19:40:07Z","timestamp":1600717207000},"page":"1117-1128","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["(+)\u2010Sesamin\u2010oxidising CYP92B14 shapes specialised lignan metabolism in sesame"],"prefix":"10.1111","volume":"104","author":[{"given":"Erisa","family":"Harada","sequence":"first","affiliation":[{"name":"Suntory Foundation for Life Sciences (SUNBOR) Bioorganic Research Institute 8\u20101\u20101 Seikadai, Seika Soraku Kyoto 619\u20100284 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7867-330X","authenticated-orcid":false,"given":"Jun","family":"Murata","sequence":"additional","affiliation":[{"name":"Suntory Foundation for Life Sciences (SUNBOR) Bioorganic Research Institute 8\u20101\u20101 Seikadai, Seika Soraku Kyoto 619\u20100284 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0238-6480","authenticated-orcid":false,"given":"Eiichiro","family":"Ono","sequence":"additional","affiliation":[{"name":"Research Institute Suntory Global Innovation Center Ltd (SIC) 8\u20101\u20101 Seikadai, Seika Soraku Kyoto 619\u20100284 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiromi","family":"Toyonaga","sequence":"additional","affiliation":[{"name":"Research Institute Suntory Global Innovation Center Ltd (SIC) 8\u20101\u20101 Seikadai, Seika Soraku Kyoto 619\u20100284 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akira","family":"Shiraishi","sequence":"additional","affiliation":[{"name":"Suntory Foundation for Life Sciences (SUNBOR) Bioorganic Research Institute 8\u20101\u20101 Seikadai, Seika Soraku Kyoto 619\u20100284 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kosuke","family":"Hideshima","sequence":"additional","affiliation":[{"name":"Graduate School of Science and Engineering University of Toyama 3190 Gofuku Toyama 930\u20108555 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masayuki P.","family":"Yamamoto","sequence":"additional","affiliation":[{"name":"Faculty of Science Academic Assembly University of Toyama 3190 Gofuku Toyama 930\u20108555 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3070-006X","authenticated-orcid":false,"given":"Manabu","family":"Horikawa","sequence":"additional","affiliation":[{"name":"Suntory Foundation for Life Sciences (SUNBOR) Bioorganic Research Institute 8\u20101\u20101 Seikadai, Seika Soraku Kyoto 619\u20100284 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,10,11]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1023\/A:1025029903549"},{"key":"e_1_2_10_3_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1201\/b13601","volume-title":"Sesame: The genus Sesamum","author":"Bedigian D.","year":"2010"},{"key":"e_1_2_10_4_1","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1201\/b13601","volume-title":"Sesame: The genus Sesamum","author":"Bedigian D.","year":"2010"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/0305-1978(85)90071-7"},{"key":"e_1_2_10_6_1","doi-asserted-by":"crossref","first-page":"348","DOI":"10.1007\/BF02640380","article-title":"Sesamin, sesamolin, and sesamol content of the oil of sesame seed as affected by strain, location grown, ageing, and frost damage","volume":"71","author":"Beroza M.","year":"1955","journal-title":"J. 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