Δ4-dn-iso-OPDA, a bioactive plant hormone of Marchantia polymorpha
Takuya Kaji,
Yuho Nishizato,
Hidenori Yoshimatsu,
Akiyoshi Yoda,
Wenting Liang,
Andrea Chini,
Gemma Fernández-Barbero,
Kei Nozawa,
Junko Kyozuka,
Roberto Solano,
Minoru Ueda
Affiliations
Takuya Kaji
Graduate School of Science, Tohoku University, 6-3, Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, Japan
Yuho Nishizato
Graduate School of Science, Tohoku University, 6-3, Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, Japan
Hidenori Yoshimatsu
Graduate School of Science, Tohoku University, 6-3, Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, Japan
Akiyoshi Yoda
Graduate School of Life Sciences, Tohoku University, 2-1-1, Katahira, Aoba-ku, Sendai 980-8577, Japan
Wenting Liang
Plant Molecular Genetics Department, National Centre for Biotechnology (CNB), Consejo Superior de Investigaciones Cientificas (CSIC), Campus University Autonoma, 28049 Madrid, Spain
Andrea Chini
Plant Molecular Genetics Department, National Centre for Biotechnology (CNB), Consejo Superior de Investigaciones Cientificas (CSIC), Campus University Autonoma, 28049 Madrid, Spain
Gemma Fernández-Barbero
Plant Molecular Genetics Department, National Centre for Biotechnology (CNB), Consejo Superior de Investigaciones Cientificas (CSIC), Campus University Autonoma, 28049 Madrid, Spain
Kei Nozawa
Graduate School of Science, Tohoku University, 6-3, Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, Japan
Junko Kyozuka
Graduate School of Life Sciences, Tohoku University, 2-1-1, Katahira, Aoba-ku, Sendai 980-8577, Japan
Roberto Solano
Plant Molecular Genetics Department, National Centre for Biotechnology (CNB), Consejo Superior de Investigaciones Cientificas (CSIC), Campus University Autonoma, 28049 Madrid, Spain
Minoru Ueda
Graduate School of Science, Tohoku University, 6-3, Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8578, Japan; Department of Molecular and Chemical Life Sciences, Graduate School of Life Sciences, Tohoku University, Sendai 980-8577, Japan; Corresponding author
Summary: Significant progress has been recently made in our understanding of the evolution of jasmonates biosynthesis and signaling. The bioactive jasmonate activating COI1-JAZ co-receptor differs in bryophytes and vascular plants. Dinor-iso-12-oxo-phytodienoic acid (dn-iso-OPDA) is the bioactive hormone in bryophytes and lycophytes. However, further studies showed that the full activation of hormone signaling in Marchantia polymorpha requires additional unidentified hormones. Δ4-dn-OPDAs were previously identified as novel bioactive jasmonates in M. polymorpha. In this paper, we describe the major bioactive isomer of Δ4-dn-OPDAs as Δ4-dn-iso-OPDA through chemical synthesis, receptor binding assay, and biological activity in M. polymorpha. In addition, we disclosed that Δ4-dn-cis-OPDA is a biosynthetic precursor of Δ4-dn-iso-OPDA. We demonstrated that in planta cis-to-iso conversion of Δ4-dn-cis-OPDA occurs in the biosynthesis of Δ4-dn-iso-OPDA, defining a key biosynthetic step in the chemical evolution of hormone structure. We predict that these findings will facilitate further understanding of the molecular evolution of plant hormone signaling.
