“…(±)-[3-OC 2 H 3 ]Arctigenins (20-d 3 ) were prepared in the same manner as the preparation of (±)-arctigenins (20) 36 but with [3-OC 2 H 3 ]-4-benzyloxy-3methoxybenzyl bromide. 33 (±)-Trachelogenins (21) were prepared in the same manner as the synthesis of wikstromol 62, 63 but with (±)-b-(3,4-dimethoxybenzyl)-c-butyrolactones prepared as previously described, 64 while (±)-[3-OC 2 H 3 ]trachelogenins (21-d 3 ) were prepared exactly as that of the unlabelled (21) but with [3-OC 2 H 3 ]-4-benzyloxy-3-methoxybenzyl bromide. 33 (±)-[3-OC (7), Y = 1.09X + 0.11, 0.05-0.37 nmol range; coniferaldehyde (8), Y = 0.92X + 0.03, 0.05-0.34 nmol range; 5-hydroxyconiferaldehyde (9), Y = 0.75X + 0.04, 0.04-0.31 nmol range; sinapaldehyde (10), Y = 0.83X + 0.07, 0.08-0.58 nmol range; p-coumaryl alcohol (11), Y = 0.76X + 0.07, 0.05-0.40 nmol range; caffeyl alcohol (12), Y = 1.44X + 0.07, 0.05-0.36 nmol range; coniferyl alcohol (13), Y = 0.26X + 0.03, 0.44-3.32 nmol range; 5-hydroxyconiferyl alcohol (14), Y = 3.96X + 0.73, 0.04-0.31 nmol range; sinapyl alcohol (15), Y = 0.72X + 0.07, 0.04-0.29 nmol range; pinoresinol (16), Y = 2.71X + 0.73, 0.28-2.09 nmol range; lariciresinol (17), Y = 1.31X + 0.36, 0.28-2.08 nmol range; secoisolariciresinol (18), Y = 0.87X + 0.14, 2.20-16.56 nmol range; matairesinol (19) -d 3 ) (0.4 mg each) were dissolved in 0.1 M KPB buffer (pH 7.0, 400.0 ll), and incubated individually with four maturing seeds (7 and 13 DAF) for 24 h. Then, the seeds were freeze-dried, powdered using a mortar and pestle, and extracted with hot MeOH.…”