Fraction C4 (100 mg) was passed over a Sephadex LH-20 column (30 mm × 800 mm, 80 g) and then eluted with MeOH (500 mL) to obtain compound 20 (15 mg). Fraction E3 (1 g) was subjected to chromatography on ODS (30 mm × 150 mm, 50 g) and then eluted successively with solvents selleck kinase inhibitor of decreasing polarity (MeOH/H2O, 4:6 600 mL−6:4 600 mL−7:3 600 mL−9:1 600 mL−1:0 600 mL) to yield seven fractions, E3-1−E3-7. Compound 21 (8 mg) was obtained as granulated crystal from E3-6. Fractions F (18 g), G (15 g), H (20 g), and I (20 g) were subjected to chromatography on ODS (50 mm ×
250 mm, 250 g) and then eluted successively with solvents of decreasing polarity (MeOH/H2O, 3:7 3 L−5:5 3 L−7:3 3 L−9:1 3 L−1:0 3 L) to yield 11 fractions, F1−F11, eight fractions, G1−G8, seven fractions, H1−H7, and
eight fractions, I1−I8. Compound 1 (10 mg) was obtained as granulated crystal from F-5. Isolation of the following 15 compounds was performed by preparative HPLC: compounds find more 2 (18 mg; tR 75.0 min), 12 (30 mg; tR 38.9 min), 13 (20 mg; tR 46.8 min), and 14 (60 mg; tR 53.5 min) were isolated from fraction D3 (500 mg) by HPLC system I; compound 18 (4 mg; tR 41.8 min) was isolated from fraction A2 (60 mg) by HPLC system VI; compounds 3 (15 mg; tR 70.3 min), 4 (15 mg; tR 45.8 min), 5 (14 mg; tR 58.9 min), and 6 (14 mg; tR 65.9 min) were isolated from fraction I4 (200 mg) by HPLC system II; compounds 7 (40 mg; tR 33.5 min) and 8 (60 mg; tR 49.6 min) were isolated from
fraction H5 (500 mg) by HPLC system III; compounds 9 (8 mg; tR 17.5 min), 10 (70 mg; tR 26.5 min), and 11 (65 mg; tR 33.7 min) were isolated from fraction G6 (1 g) by HPLC system IV; compound 19 (6 mg; tR 122.9 min) was isolated from fraction B2 (40 mg) by HPLC system V. (20S,23R)-3β-hydroxy-12β,23-epoxy-dammar-24-ene 3-mercaptopyruvate sulfurtransferase 3-O-β-D-glucopyranoside-20-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (notoginsenoside-LX): white amorphous powder; [α]20 D = −20.8 (c = 0.30, MeOH); IR νmax 3425, 2930, 1637, 1452, 1384, 1079, 620 cm−1; Libermann-Burchard and Molish reactions were positive; 1H and 13C NMR: see Table 1; HRESIMS m/z 937.5097 [M+Na]+ (calculated for C47H78O17Na, 937.5137). (20S,23R)-3β-hydroxy-12β,23-epoxy-dammar-24-ene 20-O-α-L-arabinofuranosyl -(1→6)-β-D-glucopyranoside (notoginsenoside-LY): white granulated crystal; [α]20 D = −11.4 (c = 0.45, MeOH); IR νmax 3419, 2942, 1637, 1452, 1384, 1043, 621 cm−1; Libermann-Burchard and Molish reactions were positive; 1H and 13C NMR: see Table 1; HRESIMS m/z 775.4577 (calculated for C41H68O12Na, 775.4608). 20(S)-protopanaxadiol 3-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl -(1→2)-β-D-glucopyranoside-20-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (notoginsenoside-FZ): white granulated crystal; [α]20 D = −12.2 (c = 0.