Synthesis of Carlactone Derivatives to Develop a Novel Inhibitor of Strigolactone Biosynthesis

Kojiro Kawada; Tatsuo Saito; Satoshi Onoda; Takuma Inayama; Ikuo Takahashi; Yoshiya Seto; Takahito Nomura; Yasuyuki Sasaki; Tadao Asami; Shunsuke Yajima; Shinsaku Ito

doi:10.1021/acsomega.3c00098

Synthesis of Carlactone Derivatives to Develop a Novel Inhibitor of Strigolactone Biosynthesis

ACS Omega. 2023 Apr 5;8(15):13855-13862. doi: 10.1021/acsomega.3c00098. eCollection 2023 Apr 18.

Authors

Affiliations

¹ Department of Bioscience, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo 156-8502, Japan.
² Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.
³ Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo 156-8502, Japan.
⁴ Department of Agricultural Chemistry, School of Agriculture, Meiji University, 1-1-1 Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan.
⁵ Center for Bioscience Research and Education, Utsunomiya University, 350 Mine-machi, Utsunomiya, Tochigi 321-8505, Japan.

Abstract

Strigolactones (SLs), phytohormones that inhibit shoot branching in plants, promote the germination of root-parasitic plants, such as Striga spp. and Orobanche spp., which drastically reduces the crop yield. Therefore, reducing SL production via chemical treatment may increase the crop yield. To design specific inhibitors, it is valid to utilize the substrate structure of the target proteins as lead compounds. In this study, we focused on Os900, a rice enzyme that oxidizes the SL precursor carlactone (CL) to 4-deoxyorobanchol (4DO), and synthesized 10 CL derivatives. The effects of the synthesized CL derivatives on SL biosynthesis were evaluated by the Os900 enzyme assay in vitro and by measuring 4DO levels in rice root exudates. We identified some CL derivatives that inhibited SL biosynthesis in vitro and in vivo.