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They are commonly associated with antimicrobial activity and thought to be synthesized\n                    <jats:italic>de novo<\/jats:italic>\n                    or accumulated in response to microbial pathogens. (\u2212)\u2010Maackiain is a lineage\u2010specific pterocarpan detected in some legumes, including red clover (\n                    <jats:italic>Trifolium pratense<\/jats:italic>\n                    ). The biosynthesis of (\u2212)\u2010maackiain involves the formation of a distinctive methylenedioxy bridge to convert calycosin to pseudobaptigenin, which is predicted to be catalyzed by a cytochrome P450. We integrated metabolomic and transcriptomic datasets of\n                    <jats:italic>T. pratense<\/jats:italic>\n                    roots treated with the fungal pathogens,\n                    <jats:italic>Fusarium oxysporum<\/jats:italic>\n                    (hemibiotroph) and\n                    <jats:italic>Phoma medicaginis<\/jats:italic>\n                    (necrotroph), to identify candidate P450 genes associated with pterocarpan accumulation. Fungal elicitation initiated a robust defense response via upregulation of core metabolism and over 30 isoflavonoid\u2010associated genes, including both early (chalcone\u2010flavanone) and late (pterocarpan) biosynthetic modules. These transcriptomic changes were accompanied by drastic pathogen\u2010specific divergence in metabolic profiles, featuring over 40 differentially accumulated (iso)flavonoids.\n                    <jats:italic>F. oxysporum<\/jats:italic>\n                    infection resulted in severe necrosis and markedly greater transcriptional reprogramming relative to\n                    <jats:italic>P. medicaginis<\/jats:italic>\n                    . However, the defense response to\n                    <jats:italic>P. medicaginis<\/jats:italic>\n                    was characterized by the strong accumulation of pterocarpans, including (\u2212)\u2010maackiain. Using a combination of strategies, including weighted gene co\u2010expression network analysis, candidate cytochrome P450s were selected for putative pseudobaptigenin synthase (PbS) activity. Functional characterization using biotransformation and microsomal fraction assays identified\n                    <jats:italic>T. pratense<\/jats:italic>\n                    pseudobaptigenin synthase (TpPbS\/CYP76F319), which catalyzes the conversion of calycosin to pseudobaptigenin. This discovery facilitates the reconstitution of (\u2212)\u2010maackiain biosynthesis and its future heterologous production at scale for agricultural and health applications.\n                  <\/jats:p>","DOI":"10.1111\/tpj.71018","type":"journal-article","created":{"date-parts":[[2026,7,2]],"date-time":"2026-07-02T21:49:41Z","timestamp":1783028981000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Discovery of pseudobaptigenin synthase in fungal\u2010infected\n                    <i>Trifolium pratense<\/i>\n                    roots"],"prefix":"10.1111","volume":"127","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-1610-7355","authenticated-orcid":false,"given":"Lee Marie","family":"Raytek","sequence":"first","affiliation":[{"name":"Department of Biological Sciences University of Toronto Scarborough  Toronto Ontario M1C 1A4 Canada"},{"name":"Department of Cell and Systems Biology University of Toronto  Toronto Ontario M5S 3G5 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lan","family":"Liu","sequence":"additional","affiliation":[{"name":"Food Science and Agricultural Chemistry McGill University  Sainte\u2010Anne\u2010de\u2010Bellevue Quebec H9X 3V9 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9935-6685","authenticated-orcid":false,"given":"St\u00e9phane","family":"Bayen","sequence":"additional","affiliation":[{"name":"Food Science and Agricultural Chemistry McGill University  Sainte\u2010Anne\u2010de\u2010Bellevue Quebec H9X 3V9 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5693-6324","authenticated-orcid":false,"given":"Mehran","family":"Dastmalchi","sequence":"additional","affiliation":[{"name":"Department of Biological Sciences University of Toronto Scarborough  Toronto Ontario M1C 1A4 Canada"},{"name":"Department of Cell and Systems Biology 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