HPLC on a fortis H2O column (250 × 4.6 mm, flow rate 1.0 ml min−1) using CH3CN–H2O (7:3) as the inhibitors eluent to yield compounds 5 (20 mg) and 6 (15 mg). 13C NMR (75 MHz,
CD3OD): δ 168.6, 151.0,
113.6, 99.3, 94.5, 79.7, 78.8, 78.4, 78.0, 77.5, 73.9, 70.9, 62.5, 51.8, 38.4, Selleckchem SAR405838 26.9, 21.8. Amorphous powder, [α]D25 + 41.0° (c 0.5, MeOH); IR(KBr) νmax: 3421, 1702, 1634, 1524, 1445, 1288, 1172, 1075, 865, 765 cm −1; 1H NMR (300 MHz, CD3OD): δ 7.79 (1H, d, J = 15.8 Hz, H-7″), 7.41 (1H, d, J = 1.8 Hz, VRT752271 in vitro H-2″), 7.31 (1H, s, H-3), 6.98 (2H, m), 6.54 (1H, d, J = 15.8 Hz, H-8″), 5.80 (1H, d, J = 3.9 Hz, H-1), 4.85 (1H, dd, J = 5.3 and1.7 Hz, H-7), 4.63 (1H, d, J = 7.74 Hz, H-1′), 3.86 (3H, s, OMe), 3.79 (3H, s, COOMe), 3.69 (1H, dd, J = 11.6 and 5.6 Hz, H-6′), 3.37–3.29 (4H, m), 2.91 (1H, d, J = 8. Amorphous powder, [α]D25 + 41.6° (c 0.5, MeOH); IR(KBr) νmax: 3420, 1705, 1634, 1514, 1445, 1285, 1170, 1075, 868, 765 cm −1; 1H NMR (300 MHz, CD3OD): δ 7.78 (1H, d, J = 15.8 Hz, H-7″), 7.39 (1H, d, J = 1.7 Hz, H-2″), 7.31 (1H, s, H-3), 6.98 (2H, m), 6.53 (1H, d, J = 15.8 Hz, H-8″), 5.80 (1H, d, J = 4.0 Hz, H-1), 4.85 (1H, dd, J = 5.3 and 1.8 Hz, H-7), 4.63 (1H, d, J = 7.74 Hz, Ergoloid H-1′), 3.90 (3H, s, OMe), 3.86 (3H, s, OMe), 3.79 (3H, s, COOMe), 3.69 (1H, dd, J = 11.6 and 5.6 Hz, H-6′), 3.37–3.29 (4H, m), 2.93 (1H, d, J = 8.7 Hz, H-9), 2.43 (2H m), 1.17 (3H, s, H3-10). 13C NMR (75 MHz, CD3OD): δ 168.6, 167.4, 152.1, 151.2, 150.6, 148.5, 145.3, 130.3, 129.8, 128.8, 128.1, 117.8, 99.7, 92.6, 79.5, 78.8, 78.5, 77.5, 76.3, 72.6, 69.9, 62.3, 57.6, 55.7, 55.1, 51.7, 45.6, 21.7. ESIMS: m/z 635 (M + Na)+. Amorphous powder, [α]D25 + 87.1° (c 0.5, MeOH); IR(KBr) νmax: 3424, 1703, 1634, 1514, 1445, 1288, 1170, 1075, 868, 765 cm −1; 1H NMR (300 MHz, CD3OD): δ 7.82 (1H, d, J = 15.8 Hz, H-7″), 7.69 (2H, m), 7.47–7.34 (3H, m), 7.32 (1H, s, H-3), 6.90 (1H, d, J = 15.8 Hz, H-8″), 5.71 (1H, d, J = 3.6 Hz, H-1), 4.91 (1H, dd, J = 5.1 and1.5 Hz, H-7), 4.56 (1H, d, J = 7.74 Hz, H-1′), 3.89 (3H, s, COOMe), 3.78 (2H, m), 3.42–3.10 (4H, m), 2.85 (1H, d, J = 8.