Fig. 5. Conversion of [13C]-CL to [13C]-5DS in the feeding experiment using L. japonicus roots. A) 13C-incorporation rates of (11R)- and (11S)-[1-13CH]-CL 3 into [8-13CH]-5DS. 13C-incorporation rates were cal3 culated from the formula: (peak area of m/z 332.15/ 97.00–peak area of m/z 331.15/97.00*0.20)/((peak area of 332.15/97.00–peak area of m/z 331.15/ 97.00*0.20)+peak area of m/z 331.15/97.00), where 0.20 is the ratio of peak area of 332.15/97.00 to peak area of m/z 331.15/97.00 of natural 5DS. Peak areas were measured using the MRM transition for 5DS (331.15/97.00 and 332.15/97.00 m/z in positive mode) in LC-MS/MS analysis. n = 3. B) Determination of the stereochemistry of 5DS converted from (11R)- [1-13CH]-CL. Chiral LC-MS/MS analysis of stereo3 isomers of 5DS in root exudates after feeding of (11R)- [1-13CH]-CL. MRM of synthetic standards of 5DS and 3 4DO stereoisomers and [8–13C]-(+)-5DS from L. japonicus root exudates after feeding (11R)-[1-13CH]-CL.

Published as part of Mori, Narumi, Sado, Aika, Xie, Xiaonan, Yoneyama, Kaori, Asami, Kei, Seto, Yoshiya, Nomura, Takahito, Yamaguchi, Shinjiro, Yoneyama, Koichi & Akiyama, Kohki, 2020, Chemical identification of 18-hydroxycarlactonoic acid as an LjMAX1 product and in planta conversion of its methyl ester to canonical and noncanonical strigolactones in Lotus japonicus, pp. 1-16 in Phytochemistry (112349) 174 on page 7, DOI: 10.1016/j.phytochem.2020.112349, http://zenodo.org/record/8294803