{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T08:06:36Z","timestamp":1788854796779,"version":"build-2803163510"},"reference-count":79,"publisher":"Oxford University Press (OUP)","issue":"8","license":[{"start":{"date-parts":[[2026,4,28]],"date-time":"2026-04-28T00:00:00Z","timestamp":1777334400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/pages\/standard-publication-reuse-rights"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["18H02255"],"award-info":[{"award-number":["18H02255"]}],"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":["22H02406"],"award-info":[{"award-number":["22H02406"]}],"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":["23K23671"],"award-info":[{"award-number":["23K23671"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Lignans are phenylpropanoid dimers in which the monomers are linked by the central carbon atoms of their propyl side chains. In addition to the biosynthesis of biologically active lignans, the unique stereochemical mechanisms of biosynthetic reactions have been of long-standing interest. The enantiomeric composition of pinoresinol and lariciresinol\u2014the two lignans farthest upstream in the lignan biosynthetic pathway\u2014varies greatly among the plant species; these compounds are not enantiomerically pure and are mixtures of both enantiomers. The enantiomeric composition of the next intermediate, secoisolariciresinol, also varies by plant species, with some being enantiomerically pure. Conversely, the next compound, matairesinol, is always enantiomerically pure. In most cases, it is levorotatory, while the opposite dextrorotatory enantiomer, (+)-matairesinol, has been obtained from Thymelaeaceae plants, including Daphne genkwa. The conversion of pinoresinol to secoisolariciresinol via lariciresinol is catalyzed by pinoresinol\/lariciresinol reductases (PLRs). Secoisolariciresinol is then oxidized by secoisolariciresinol dehydrogenases (SIRDs) to afford matairesinol. Many PLRs from various plant species preferentially reduce (+)-pinoresinol to (\u2212)-secoisolariciresinol, while others preferentially reduce (\u2212)-pinoresinol to (+)-secoisolariciresinol. However, the specific formation and accumulation of (+)-matairesinol in Thymelaeaceae plants remained unknown. This study demonstrates that DgPLRs selectively reduce (\u2212)-lariciresinol but not (+)-lariciresinol, resulting in the formation of (+)-secoisolariciresinol. Furthermore, DgSIRDs were found to selectively oxidize (+)-secoisolariciresinol over (\u2212)-secoisolariciresinol, yielding (+)-matairesinol. Thus, the selectivity of DgPLRs for lariciresinol enantiomers, rather than pinoresinol enantiomers and the selectivity of DgSIRDs for secoisolariciresinol enantiomers, are responsible for the accumulation of nearly enantiomerically pure (+)-secoisolariciresinol and enantiomerically pure (+)-matairesinol in D. genkwa.<\/jats:p>","DOI":"10.1093\/pcp\/pcag054","type":"journal-article","created":{"date-parts":[[2026,4,24]],"date-time":"2026-04-24T11:42:17Z","timestamp":1777030937000},"page":"1328-1345","source":"Crossref","is-referenced-by-count":0,"title":["Pinoresinol\/lariciresinol reductases and secoisolariciresinol dehydrogenases involved in the specific production of (+)-enantiomer of matairesinol in\n                    <i>Daphne genkwa<\/i>"],"prefix":"10.1093","volume":"67","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3116-3323","authenticated-orcid":false,"given":"Fernando Satoshi","family":"Tutihashi","sequence":"first","affiliation":[{"name":"Research Institute for Sustainable Humanosphere, Kyoto University , Gokasho, Uji, Kyoto 611-0011 ,","place":["Japan"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mitsuki","family":"Hirota","sequence":"additional","affiliation":[{"name":"Research Institute for Sustainable Humanosphere, Kyoto University , Gokasho, Uji, Kyoto 611-0011 ,","place":["Japan"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1204-9229","authenticated-orcid":false,"given":"Masaomi","family":"Yamamura","sequence":"additional","affiliation":[{"name":"Research Institute for Sustainable Humanosphere, Kyoto University , Gokasho, Uji, Kyoto 611-0011 ,","place":["Japan"]},{"name":"Faculty of Bioscience and Bioindustry, Tokushima University , Minami-josanjima-cho 2-1, Tokushima 770-8502 ,","place":["Japan"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keisuke","family":"Kobayashi","sequence":"additional","affiliation":[{"name":"Research Institute for Sustainable Humanosphere, Kyoto University , Gokasho, Uji, Kyoto 611-0011 ,","place":["Japan"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takefumi","family":"Hattori","sequence":"additional","affiliation":[{"name":"Faculty of Bioscience and Bioindustry, Tokushima University , Minami-josanjima-cho 2-1, Tokushima 770-8502 ,","place":["Japan"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7578-7392","authenticated-orcid":false,"given":"Yuki","family":"Tobimatsu","sequence":"additional","affiliation":[{"name":"Research Institute for Sustainable Humanosphere, Kyoto University , Gokasho, Uji, Kyoto 611-0011 ,","place":["Japan"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bj\u00f6rn Robert","family":"Hamberger","sequence":"additional","affiliation":[{"name":"Department of Biochemistry & Molecular Biology, Michigan State University , 603 Wilson Road, East Lansing, MI 48824 ,","place":["USA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1135-5387","authenticated-orcid":false,"given":"Toshiaki","family":"Umezawa","sequence":"additional","affiliation":[{"name":"Research Institute for Sustainable Humanosphere, Kyoto University , Gokasho, Uji, Kyoto 611-0011 ,","place":["Japan"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2026,4,28]]},"reference":[{"key":"2026090803063573900_ref1","doi-asserted-by":"publisher","first-page":"1745","DOI":"10.1271\/bbb.70168","article-title":"Antimicrobiological activity of lignan: effect of benzylic oxygen and stereochemistry of 2,3-dibenzyl-4-butanolide and 3,4-dibenzyltetrahydrofuran lignans on activity","volume":"71","author":"Akiyama","year":"2007","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"2026090803063573900_ref2","doi-asserted-by":"publisher","first-page":"79","DOI":"10.1177\/1934578X1400900123","article-title":"Antiausterity activity of arctigenin enantiomers: importance of (2R,3R)-absolute configuration","volume":"9","author":"Awale","year":"2014","journal-title":"Nat. Prod. Commun."},{"key":"2026090803063573900_ref3","doi-asserted-by":"publisher","first-page":"810","DOI":"10.1111\/j.1365-313X.2008.03558.x","article-title":"Hinokinin biosynthesis in Linum corymbulosum Reichenb","volume":"55","author":"Bayindir","year":"2008","journal-title":"Plant J."},{"key":"2026090803063573900_ref4","doi-asserted-by":"publisher","first-page":"248","DOI":"10.1016\/0003-2697(76)90527-3","article-title":"A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding","volume":"72","author":"Bradford","year":"1976","journal-title":"Anal. Biochem."},{"key":"2026090803063573900_ref5","doi-asserted-by":"publisher","first-page":"104155","DOI":"10.1016\/j.arabjc.2022.104155","article-title":"Arylnaphthalide lignans from Saussurea medusa and their anti-inflammatory activities","volume":"15","author":"Cao","year":"2022","journal-title":"Arab. J. Chem."},{"key":"2026090803063573900_ref6","doi-asserted-by":"publisher","first-page":"197","DOI":"10.1515\/hf-2018-0026","article-title":"The gene expression and enzymatic activity of pinoresinol-lariciresinol reductase during wood formation in Taiwania cryptomerioides Hayata","volume":"73","author":"Chiang","year":"2019","journal-title":"Holzforschung"},{"key":"2026090803063573900_ref7","doi-asserted-by":"publisher","first-page":"27026","DOI":"10.1016\/S0021-9258(19)74213-6","article-title":"Stereospecificity of (+)-pinoresinol and (+)-lariciresinol reductases from Forsythia intermedia","volume":"268","author":"Chu","year":"1993","journal-title":"J. Biol. Chem."},{"key":"2026090803063573900_ref8","doi-asserted-by":"publisher","first-page":"405","DOI":"10.1007\/s00425-017-2701-0","article-title":"Functional characterization of the pinoresinol\u2013lariciresinol reductase-2 gene reveals its roles in yatein biosynthesis and flax defense response","volume":"246","author":"Corbin","year":"2017","journal-title":"Planta"},{"key":"2026090803063573900_ref9","doi-asserted-by":"publisher","first-page":"1890","DOI":"10.1016\/j.phytochem.2008.04.002","article-title":"Trypanocidal structure-activity relationship for cis- and trans-methylpluviatolide","volume":"69","author":"Silva","year":"2008","journal-title":"Phytochemistry"},{"key":"2026090803063573900_ref10","doi-asserted-by":"publisher","first-page":"362","DOI":"10.1126\/science.275.5298.362","article-title":"Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center","volume":"275","author":"Davin","year":"1997","journal-title":"Science"},{"key":"2026090803063573900_ref11","doi-asserted-by":"publisher","first-page":"3091","DOI":"10.1021\/acssynbio.0c00354","article-title":"Assembly of plant enzymes in E. coli for the production of the valuable (\u2212)-podophyllotoxin precursor (\u2212)-pluviatolide","volume":"9","author":"Decembrino","year":"2020","journal-title":"ACS Synth. Biol."},{"key":"2026090803063573900_ref12","doi-asserted-by":"publisher","first-page":"29473","DOI":"10.1074\/jbc.271.46.29473","article-title":"(+)-Pinoresinol\/(+)-lariciresinol reductase from Forsythia intermedia. Protein purification, cDNA cloning, heterologous expression and comparison to isoflavone reductase","volume":"271","author":"Dinkova-Kostova","year":"1996","journal-title":"J. Biol. Chem."},{"key":"2026090803063573900_ref13","doi-asserted-by":"publisher","first-page":"38","DOI":"10.1016\/j.jmgm.2013.08.008","article-title":"Elucidating binding modes of zuonin A enantiomers to JNK1 via in silico methods","volume":"45","author":"Dykstra","year":"2013","journal-title":"J. Mol. Graph. Model."},{"key":"2026090803063573900_ref14","doi-asserted-by":"publisher","first-page":"114053","DOI":"10.1016\/j.phytochem.2024.114053","article-title":"Effect of pinoresinol-lariciresinol reductases on biosynthesis of lignans with substrate selectivity in Schisandra chinensis","volume":"221","author":"Feng","year":"2024","journal-title":"Phytochemistry"},{"key":"2026090803063573900_ref15","doi-asserted-by":"publisher","first-page":"618","DOI":"10.1074\/jbc.274.2.618","article-title":"Recombinant pinoresinol-lariciresinol reductases from western red cedar (Thuja plicata) catalyze opposite enantiospecific conversions","volume":"274","author":"Fujita","year":"1999","journal-title":"J. Biol. Chem."},{"key":"2026090803063573900_ref16","doi-asserted-by":"publisher","first-page":"143","DOI":"10.1016\/S1074-5521(99)89006-1","article-title":"Regiochemical control of monolignol radical coupling: a new paradigm for lignin and lignan biosynthesis","volume":"6","author":"Gang","year":"1999","journal-title":"Chem. Biol."},{"key":"2026090803063573900_ref17","doi-asserted-by":"publisher","first-page":"443","DOI":"10.1002\/prot.25666","article-title":"The short-chain dehydrogenase\/reductase engineering database (SDRED): a classification and analysis system for a highly diverse enzyme family","volume":"87","author":"Gr\u00e4ff","year":"2019","journal-title":"Proteins"},{"key":"2026090803063573900_ref18","doi-asserted-by":"publisher","first-page":"321","DOI":"10.1023\/B:PHYT.0000045494.98645.a3","article-title":"Biological activities of lignans and stilbenoids associated with plant-insect chemical interactions","volume":"2","author":"Harmatha","year":"2003","journal-title":"Phytochem. Rev."},{"key":"2026090803063573900_ref19","doi-asserted-by":"publisher","first-page":"603","DOI":"10.1016\/j.febslet.2007.01.018","article-title":"(+)-Pinoresinol\/(\u2212)-lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B","volume":"581","author":"Hemmati","year":"2007","journal-title":"FEBS Lett."},{"key":"2026090803063573900_ref20","doi-asserted-by":"publisher","first-page":"928","DOI":"10.1055\/s-0030-1250036","article-title":"Pinoresinol-lariciresinol reductases with opposite enantiospecificity determine the enantiomeric composition of lignans in the different organs of Linum usitatissimum L","volume":"76","author":"Hemmati","year":"2010","journal-title":"Planta Med."},{"key":"2026090803063573900_ref21","doi-asserted-by":"publisher","first-page":"1011","DOI":"10.1039\/D0NP00010H","article-title":"Regio- and stereoselective intermolecular phenol coupling enzymes in secondary metabolite biosynthesis","volume":"38","author":"H\u00fcttel","year":"2021","journal-title":"Nat. Prod. Rep."},{"key":"2026090803063573900_ref22","first-page":"580","article-title":"Biosynthesis and stereochemistry of lignans in Zanthoxylum ailanthoides I. (+)-lariciresinol formation by enzymic reduction of (\u00b1)-pinoresinols","volume":"43","author":"Katayama","year":"1997","journal-title":"Mokuzai Gakkaishi"},{"key":"2026090803063573900_ref23","doi-asserted-by":"publisher","first-page":"243","DOI":"10.1016\/S0031-9422(99)00004-7","article-title":"Identification of Thuja occidentalis lignans and its biosynthetic relationship","volume":"51","author":"Kawai","year":"1999","journal-title":"Phytochemistry"},{"key":"2026090803063573900_ref24","doi-asserted-by":"publisher","first-page":"e100221191294","DOI":"10.2174\/2210315511666210210160903","article-title":"Aryltetralin-type lignan of podophyllum: a comprehensive review","volume":"12","author":"Kumar","year":"2022","journal-title":"Nat. Prod. J."},{"key":"2026090803063573900_ref25","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1093\/molbev\/msae263","article-title":"MEGA12: molecular evolutionary genetic analysis version 12 for adaptive and green computing","volume":"41","author":"Kumar","year":"2024","journal-title":"Mol. Biol. Evol."},{"key":"2026090803063573900_ref26","doi-asserted-by":"publisher","first-page":"2687","DOI":"10.1128\/AEM.03397-13","article-title":"Bioconversion of pinoresinol into matairesinol by use of recombinant Escherichia coli","volume":"80","author":"Kuo","year":"2014","journal-title":"Appl. Environ. Microbiol."},{"key":"2026090803063573900_ref27","doi-asserted-by":"publisher","first-page":"1224","DOI":"10.1126\/science.aac7202","article-title":"Six enzymes from mayapple that complete the biosynthetic pathway to the etoposide aglycone","volume":"349","author":"Lau","year":"2015","journal-title":"Science"},{"key":"2026090803063573900_ref28","doi-asserted-by":"publisher","first-page":"2270","DOI":"10.13345\/j.cjb.240017","article-title":"Cloning and functional characterization of the pinoresinol-lariciresinol reductase gene IiPLR2 in Isatis indigotica","volume":"40","author":"Li","year":"2024","journal-title":"Chin. J. Biotechnol."},{"key":"2026090803063573900_ref29","doi-asserted-by":"publisher","first-page":"168","DOI":"10.1055\/s-2006-959443","article-title":"Phenolic constituents of Selaginella doederleinii","volume":"60","author":"Lin","year":"1994","journal-title":"Planta Med."},{"key":"2026090803063573900_ref30","doi-asserted-by":"publisher","first-page":"427","DOI":"10.5246\/jcps.2013.05.062","article-title":"Chemical constituents from Qianliang tea","volume":"22","author":"Liu","year":"2013","journal-title":"J. Chin. Pharm. Sci."},{"key":"2026090803063573900_ref31","doi-asserted-by":"publisher","first-page":"4254","DOI":"10.1021\/acs.joc.1c03085","article-title":"Total asymmetric synthesis and stereochemical confirmation of (+)- and (\u2212)-lyoniresinol and its deuterated analogues","volume":"87","author":"Luong","year":"2022","journal-title":"J. Org. Chem."},{"key":"2026090803063573900_ref32","doi-asserted-by":"publisher","first-page":"1207","DOI":"10.1016\/S0031-9422(00)80428-8","article-title":"Biological activities of lignans","volume":"23","author":"MacRae","year":"1984","journal-title":"Phytochemistry"},{"key":"2026090803063573900_ref33","doi-asserted-by":"publisher","first-page":"1695","DOI":"10.1007\/s00425-019-03137-y","article-title":"Pinoresinol-lariciresinol reductases, key to the lignan synthesis in plants","volume":"249","author":"Markulin","year":"2019","journal-title":"Planta"},{"key":"2026090803063573900_ref34","doi-asserted-by":"publisher","first-page":"101","DOI":"10.1016\/bs.mie.2023.02.025","article-title":"Dirigent protein subfamily function and structure in terrestrial plant phenol metabolism","volume":"683","author":"Meng","year":"2023","journal-title":"Methods Enzymol."},{"key":"2026090803063573900_ref35","doi-asserted-by":"publisher","first-page":"440","DOI":"10.1007\/BF00770707","article-title":"Lignans of Linum flavum var. compactum","volume":"48","author":"Mikame","year":"2002","journal-title":"J. Wood Sci."},{"key":"2026090803063573900_ref36","doi-asserted-by":"publisher","first-page":"50714","DOI":"10.1074\/jbc.M308493200","article-title":"Crystal structures of pinoresinol-lariciresinol and phenylcoumaran benzylic ether reductases and their relationship to isoflavone reductases","volume":"278","author":"Min","year":"2003","journal-title":"J. Biol. Chem."},{"key":"2026090803063573900_ref37","doi-asserted-by":"publisher","first-page":"1493","DOI":"10.1351\/pac200072081493","article-title":"Nomenclature of lignans and neolignans (IUPAC recommendations 2000)","volume":"72","author":"Moss","year":"2000","journal-title":"Pure Appl. Chem."},{"key":"2026090803063573900_ref38","doi-asserted-by":"publisher","first-page":"175089","DOI":"10.1016\/j.ejphar.2022.175089","article-title":"A comprehensive insight into the antineoplastic activities and molecular mechanisms of deoxypodophyllotoxin: recent trends, challenges, and future outlook","volume":"928","author":"Mottaghi","year":"2022","journal-title":"Eur. J. Pharmacol."},{"key":"2026090803063573900_ref39","doi-asserted-by":"publisher","first-page":"114145","DOI":"10.1016\/j.biopha.2022.114145","article-title":"Podophyllotoxin and its derivatives: potential anticancer agents of natural origin in cancer chemotherapy","volume":"158","author":"Motyka","year":"2023","journal-title":"Biomed. Pharmacother."},{"key":"2026090803063573900_ref40","doi-asserted-by":"publisher","first-page":"76","DOI":"10.1186\/s43088-022-00256-6","article-title":"Lignans: a versatile source of anticancer drugs","volume":"11","author":"Mukhija","year":"2022","journal-title":"Beni-Suef Univ. J. Basic Appl. Sci."},{"key":"2026090803063573900_ref41","doi-asserted-by":"publisher","first-page":"15550","DOI":"10.1074\/jbc.M801131200","article-title":"Characterization of Arabidopsis thaliana pinoresinol reductase, a new type of enzyme involved in lignan biosynthesis","volume":"283","author":"Nakatsubo","year":"2008","journal-title":"J. Biol. Chem."},{"key":"2026090803063573900_ref42","doi-asserted-by":"publisher","first-page":"234","DOI":"10.1007\/BF00776455","article-title":"Enantiomeric compositions and biosynthesis of Wikstroemia sikokiana lignans","volume":"46","author":"Okunishi","year":"2000","journal-title":"J. Wood Sci."},{"key":"2026090803063573900_ref43","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1007\/BF00766790","article-title":"Isolation and enzymatic formation of lignans of Daphne genkwa and Daphne odora","volume":"47","author":"Okunishi","year":"2001","journal-title":"J. Wood Sci."},{"key":"2026090803063573900_ref44","doi-asserted-by":"publisher","first-page":"77","DOI":"10.1007\/s10086-003-0516-z","article-title":"Stereochemistry of matairesinol formation by Daphne secoisolariciresinol dehydrogenase","volume":"50","author":"Okunishi","year":"2004","journal-title":"J. Wood Sci."},{"key":"2026090803063573900_ref45","doi-asserted-by":"publisher","first-page":"643","DOI":"10.1016\/S0031-9422(00)95149-5","article-title":"Formation of (\u2212)-arctigenin in Forsythia intermedia","volume":"32","author":"Ozawa","year":"1993","journal-title":"Phytochemistry"},{"key":"2026090803063573900_ref46","doi-asserted-by":"publisher","first-page":"3287","DOI":"10.1093\/jxb\/erx141","article-title":"Dirigent proteins in plants: modulating cell wall metabolism during abiotic and biotic stress exposure","volume":"68","author":"Paniagua","year":"2017","journal-title":"J. Exp. Bot."},{"key":"2026090803063573900_ref47","doi-asserted-by":"publisher","first-page":"307","DOI":"10.1016\/j.bmcl.2014.11.045","article-title":"Enantioselective induction of SIRT1 gene by syringaresinol from Panax ginseng berry and Acanthopanax senticosus Harms stem","volume":"25","author":"Park","year":"2015","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"2026090803063573900_ref48","doi-asserted-by":"publisher","first-page":"937","DOI":"10.1016\/S1875-5364(24)60725-9","article-title":"Chiral resolution of furofuran lignans and their derivatives from the stems of Dendrobium 'Sonia'","volume":"22","author":"Qiu","year":"2024","journal-title":"Chin. J. Nat. Med."},{"key":"2026090803063573900_ref49","doi-asserted-by":"publisher","first-page":"375","DOI":"10.5511\/plantbiotechnology.13.0527b","article-title":"A novel O-methyltransferase involved in the first methylation step of yatein biosynthesis from matairesinol in Anthriscus sylvestris","volume":"30","author":"Ragamustari","year":"2013","journal-title":"Plant Biotechnol."},{"key":"2026090803063573900_ref50","doi-asserted-by":"publisher","first-page":"257","DOI":"10.5511\/plantbiotechnology.14.0722a","article-title":"Substrate-enantiomer selectivity of matairesinol O-methyltransferases","volume":"31","author":"Ragamustari","year":"2014","journal-title":"Plant Biotechnol."},{"key":"2026090803063573900_ref51","doi-asserted-by":"publisher","first-page":"2474","DOI":"10.1039\/b304411d","article-title":"Biosynthesis of yatein in Anthriscus sylvestris. Org","volume":"1","author":"Sakakibara","year":"2003","journal-title":"Biomol. Chem."},{"key":"2026090803063573900_ref52a","doi-asserted-by":"publisher","DOI":"10.1515\/znc-2008-1-203","volume":"63c","author":"","journal-title":"Z. Naturforsch."},{"key":"2026090803063573900_ref52","doi-asserted-by":"publisher","first-page":"4568","DOI":"10.4268\/cjcmm20162414","article-title":"Cloning, expression and functional identification of secoisolariciresinol dehydrogenase gene from Dysosma versipellis callus","volume":"41","author":"Shen","year":"2016","journal-title":"China J. Chin. Mater. Med."},{"key":"2026090803063573900_ref53","doi-asserted-by":"publisher","first-page":"1856","DOI":"10.1039\/D2NP00028H","article-title":"Biosynthesis, total synthesis, and pharmacological activities of aryltetralin-type lignan podophyllotoxin and its derivatives","volume":"39","author":"Shen","year":"2022","journal-title":"Nat. Prod. Rep."},{"key":"2026090803063573900_ref54","doi-asserted-by":"publisher","first-page":"1035121","DOI":"10.3389\/fpls.2022.1035121","article-title":"Identification and investigation of a novel NADP+-dependent secoisolariciresinol dehydrogenase from Isatis indigotica","volume":"13","author":"Shi","year":"2022","journal-title":"Front. Plant Sci."},{"key":"2026090803063573900_ref55","doi-asserted-by":"publisher","first-page":"e202402071","DOI":"10.1002\/cbdv.202402071","article-title":"Isolation of novel compounds from Lepidium sativum seeds and evaluation of their potential anti-tumor activity","volume":"22","author":"Shybyray","year":"2025","journal-title":"Chem. Biodivers."},{"key":"2026090803063573900_ref56","doi-asserted-by":"publisher","first-page":"1468","DOI":"10.1271\/bbb.62.1468","article-title":"Stereochemical difference in secoisolariciresinol formation between cell-free extracts from petioles and from ripening seeds of Arctium lappa L","volume":"62","author":"Suzuki","year":"1998","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"2026090803063573900_ref57","doi-asserted-by":"publisher","first-page":"1262","DOI":"10.1271\/bbb.66.1262","article-title":"Stereochemical diversity in lignan biosynthesis of Arctium lappa L","volume":"66","author":"Suzuki","year":"2002","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"2026090803063573900_ref58","doi-asserted-by":"publisher","first-page":"476","DOI":"10.1007\/BF00767901","article-title":"Lignans of Chamaecyparis obtusa","volume":"47","author":"Takaku","year":"2001","journal-title":"J. Wood Sci."},{"key":"2026090803063573900_ref59","doi-asserted-by":"publisher","first-page":"371","DOI":"10.1023\/B:PHYT.0000045487.02836.32","article-title":"Diversity in lignan biosynthesis","volume":"2","author":"Umezawa","year":"2003","journal-title":"Phytochem. Rev."},{"key":"2026090803063573900_ref60","first-page":"27","article-title":"Phylogenetic distribution of lignan producing plants","volume":"90","author":"Umezawa","year":"2003","journal-title":"Wood Res."},{"key":"2026090803063573900_ref61","first-page":"231","article-title":"Syntheses of (\u00b1)-lariciresinols","volume":"40","author":"Umezawa","year":"1994","journal-title":"Mokuzai Gakkaishi"},{"key":"2026090803063573900_ref62","first-page":"180","article-title":"Enantiomeric composition of (\u2212)-pinoresinol, (+)-matairesinol and (+)-wikstromol isolated from Wikstroemia sikokiana","volume":"42","author":"Umezawa","year":"1996","journal-title":"Mokuzai Gakkaishi"},{"key":"2026090803063573900_ref63","doi-asserted-by":"publisher","first-page":"736","DOI":"10.1271\/bbb.60.736","article-title":"Formation of the lignan (+)-secoisolariciresinol by cell-free extracts of Arctium lappa","volume":"60","author":"Umezawa","year":"1996","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"2026090803063573900_ref64","doi-asserted-by":"publisher","first-page":"10210","DOI":"10.1016\/S0021-9258(18)99211-2","article-title":"Formation of lignans (\u2212)-secoisolariciresinol and (\u2212)-matairesinol with Forsythia intermedia cell-free extracts","volume":"266","author":"Umezawa","year":"1991","journal-title":"J. Biol. Chem."},{"key":"2026090803063573900_ref65","first-page":"507","volume-title":"Biotechnology in Pulp and Paper Industry","author":"Umezawa","year":"1992"},{"key":"2026090803063573900_ref66","doi-asserted-by":"publisher","first-page":"230","DOI":"10.1271\/bbb.58.230","article-title":"Enantioselective lignan synthesis by cell-free extracts of Forsythia koreana","volume":"58","author":"Umezawa","year":"1994","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"2026090803063573900_ref67","first-page":"62","article-title":"Stereochemical diversity in lignan biosynthesis","volume":"84","author":"Umezawa","year":"1997","journal-title":"Wood Res."},{"key":"2026090803063573900_ref68","doi-asserted-by":"publisher","first-page":"97","DOI":"10.5511\/plantbiotechnology.12.1230a","article-title":"A lignan O-methyltransferase catalyzing the regioselective methylation of matairesinol in Carthamus tinctorius","volume":"30","author":"Umezawa","year":"2013","journal-title":"Plant Biotechnol."},{"key":"2026090803063573900_ref69","doi-asserted-by":"publisher","first-page":"1254","DOI":"10.1016\/j.phytochem.2005.04.026","article-title":"Pinoresinol-lariciresinol reductases with different stereospecificity from Linum album and Linum usitatissimum","volume":"66","author":"Heimendahl","year":"2005","journal-title":"Phytochemistry"},{"key":"2026090803063573900_ref70","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.phytochem.2019.02.003","article-title":"A variable loop involved in the substrate selectivity of pinoresinol\/lariciresinol reductase from Camellia sinensis","volume":"162","author":"Wu","year":"2019","journal-title":"Phytochemistry"},{"key":"2026090803063573900_ref71","doi-asserted-by":"publisher","first-page":"12614","DOI":"10.1074\/jbc.M008622200","article-title":"Secoisolariciresinol dehydrogenase purification, cloning, and functional expression implications for human health protection","volume":"276","author":"Xia","year":"2001","journal-title":"J. Biol. Chem."},{"key":"2026090803063573900_ref72","doi-asserted-by":"publisher","first-page":"6259","DOI":"10.1093\/jxb\/erv333","article-title":"Combined transcriptome and metabolite profiling reveals that IiPLR1 plays an important role in lariciresinol accumulation in Isatis indigotica","volume":"66","author":"Xiao","year":"2015","journal-title":"J. Exp. Bot."},{"key":"2026090803063573900_ref73","doi-asserted-by":"publisher","first-page":"2828","DOI":"10.1038\/s41467-021-23095-y","article-title":"Structure-based engineering of substrate specificity for pinoresinol-lariciresinol reductases","volume":"12","author":"Xiao","year":"2021","journal-title":"Nat. Commun."},{"key":"2026090803063573900_ref74","doi-asserted-by":"publisher","first-page":"105216","DOI":"10.1016\/j.fitote.2022.105216","article-title":"Lignans with neuroprotective activity from the fruits of Crataegus pinnatifida","volume":"160","author":"Xin","year":"2022","journal-title":"Fitoterapia"},{"key":"2026090803063573900_ref75","doi-asserted-by":"publisher","first-page":"124","DOI":"10.1093\/pcp\/pcac164","article-title":"Two O-methyltransferases from phylogenetically unrelated cow parsley (Anthriscus sylvestris) and hinoki-asunaro (Thujopsis dolabrata var. hondae) as a signature of lineage-specific evolution in lignan biosynthesis","volume":"64","author":"Yamamura","year":"2023","journal-title":"Plant Cell Physiol."},{"key":"2026090803063573900_ref76","doi-asserted-by":"publisher","first-page":"2942","DOI":"10.1271\/bbb.60353","article-title":"Effect of benzylic oxygen on the cytotoxic activity for colon 26 cell line of phenolic lignans","volume":"70","author":"Yamauchi","year":"2006","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"2026090803063573900_ref77","doi-asserted-by":"publisher","first-page":"104284","DOI":"10.1016\/j.phrs.2019.104284","article-title":"Lignans and neolignans: plant secondary metabolites as a reservoir of biologically active substances","volume":"146","author":"Z\u00e1le\u0161\u00e1k","year":"2019","journal-title":"Pharmacol. Res."},{"key":"2026090803063573900_ref78","doi-asserted-by":"publisher","first-page":"12998","DOI":"10.3390\/ijms222312998","article-title":"Regulation of cytosolic pH: the contributions of plant plasma membrane H+-ATPases and multiple transporters","volume":"22","author":"Zhou","year":"2021","journal-title":"Int. J. Mol. Sci."}],"container-title":["Plant and Cell Physiology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/academic.oup.com\/pcp\/advance-article-pdf\/doi\/10.1093\/pcp\/pcag054\/68178111\/pcag054.pdf","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/pcp\/article-pdf\/67\/8\/1328\/68178111\/pcag054.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/pcp\/article-pdf\/67\/8\/1328\/68178111\/pcag054.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T07:06:48Z","timestamp":1788851208000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/pcp\/article\/67\/8\/1328\/8664012"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,4,28]]},"references-count":79,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2026,4,28]]},"published-print":{"date-parts":[[2026,9,5]]}},"URL":"https:\/\/doi.org\/10.1093\/pcp\/pcag054","relation":{},"ISSN":["0032-0781","1471-9053"],"issn-type":[{"value":"0032-0781","type":"print"},{"value":"1471-9053","type":"electronic"}],"subject":[],"published-other":{"date-parts":[[2026,8]]},"published":{"date-parts":[[2026,4,28]]}}}