Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. IV. Studies on the Homoisoflavonoids of the Subterranean Part of Ophiopogon ohwii OKUYAMA and O. jaburan (KUNTH) LODD

Six homoisoflavonoidal compounds, tentatively named NE-I (1), NE-II (2), NE-III (3), NE-IV (4), NE-V (5) and NE-VI (6), were isolated from the ether-soluble fraction of the subterranean part of Ophiopogon ohwii OKUYAMA (Liliaceae) and four homoisoflavonoidal compounds, tentatively named JE-I (7), JE-II (8), JE-III (9) and JE-IV (10), were isolated from that of O. jaburan (KUNTH) LODD. NE-I and NE-II were identified as compound I (1) and compound II (2), respectively, which had been isolated by Kaneda et al. from an Ophiopogonis Tuber imported from China. NE-III, NE-IV and NE-V were identified as methylophiopogonanone A (3), methylophiopogonanone B (4) and methylophiopogonone A (5), respectively. The structures of NE-VI, JE-I, JE-II, JE-III and JE-IV were elucidated to be 5, 7-dihydroxy-6, 8-dimethyl-3-(2-hydroxy-3, 4-methylenedioxybenzyl) chromone (6), 3, 5-dihydroxy-7-methoxy-6-methyl-3-(4-hydroxybenzyl) chroman-4-one (7), 5-hydroxy-7-methoxy-6-methyl-3-(3, 4-dihydroxybenzyl) chromone (8), 5, 7-dihydroxy-6-methyl-3-(4-hydroxybenzyl) chromone (9), and 5, 7-dihydroxy-3-(4-hydroxybenzyl) chromone (10), respectively.