Molecules 2019, 24, 1113
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4.33 (1H, d, J = 2 Hz, H-1′b); 2.5 (1H, s, H-3′). 13C-NMR (δ = ppm, 150M Hz): 41.6 (C-1); 35.1 (C-2); 66.5
(C-3); 83.9 (C-4); 44.2 (C-5); 40.7 (C-6); 38.0 (C-7); 79.9 (C-8); 36.4 (C-9); 30.2 (C-10); 140.2 (C-11); 169.8
(C-12); 122.7 (C-13); 16.6 (C-14); 18.8 (C-15); 58.5 (C-1′); 75.2 (C-2′); 80.0 (C-3′). HRMS-ES (m/z): [M +
Na]+: Calcd. for C18H24O4Na: 327.1572; found 327.1574.
Compound 9: White solid, m.p.: 125–126 °C. [α]2D0: +59.0 (c 5.73; CHCl3). IR (KBr; υmax: cm−1): 3431,
1
2927, 2355, 2119, 1759, 1387, 1273, 1088, 997. H-NMR (δ = ppm, 600M Hz): 1.48 (1H, m, H-1);
1.74–1.85 (1H, m, H-2a); 2.055–2.12 (1H, m, H-2b); 4.25 (1H, m, H-3); 3.62 (1H, d, J = 7 Hz, H-4); 1.60
(1H, t, J = 15 Hz, H-6a); 1.97–2.04 (1H, m, H-6b); 3.18 (1H, m, H-7); 4.69 (1H, ddd, J = 8 and 11 Hz,
H-8); 1.74–1.85 (1H, m, H-9a); 2.16–2.22 (1H, m, H-9b); 1.97–2.04 (1H, m, H-10); 5.58 (1H, s, H-13);
6.26 (1H, s, H-13′); 1.05 (3H, d, J = 7 Hz, H-14); 1.04 (3H, s, H-15); 4.43 (1H, d, J = 16 Hz, H-1′a); 4.30
(1H, d, J = 1 6 Hz, H-1′b); 2.46 (1H, brs, H-3′); 4.22 (1H, d, J = 16 Hz, H-1″a); 4.16 (1H, d, J = 16 Hz,
H-1″b); 2.42 (1H, brs, H-3″). 13C-NMR (δ = ppm, 150M Hz): 41.4 (C-1); 32.9 (C-2); 72.2 (C-3); 81.7 (C-4);
44.0 (C-5); 40.1 (C-6); 37.8 (C-7); 79.8 (C-8); 36.4 (C-9); 30.2 (C-10); 140.0 (C-11); 169.7 (C-12); 122.6
(C-13); 16.6 (C-14); 18.4 (C-15); (57.0C-1′); 80.2 (C-2′); 74.5 (C-3′); 56.4 (C-1″); 79.7 (C-2″); 74.3 (C-3″)
HRMS-ES (m/z): [M + Na]+: Calcd. for C21H26O4Na: 365.1729; found 365.1729.
Compound 10: White amorphous solid, m.p.: 74–75 °C. [α]2D0: +10.5 (c 3.80; CHCl3). IR (KBr; υmax:
cm−1): 3433, 2924, 2360, 1757, 1637, 1456, 1205, 1076, 725. 1H-NMR (δ = ppm, 600M Hz): 1.41–1.45 (1H,
m, H-1); 1.72–1.79 (1H, m, H-2a); 2.07–2.11 (1H, m, H-2b); 4.15 (1H, m, H-3); 3.52 (1H, d, J = 7 Hz,
H-4); 1.51 (1H, t, J = 15 Hz, H-6a); 1.68 (1H, dd, J = 15 Hz, H-6b); 3.07 (1H, m, H-7); 4.64 (1H, ddd, J = 3
and 8- Hz, H8); 1.72–1.79 (1H, m, H-9a); 2.13–2.19 (1H, m, H-9b); 1.94–1.99 (1H, m, H-10); 5.43 (1H, d,
J = 2 Hz, H-13); 6.2 (1H, d, J = 2 Hz, H-13′); 1.03 (3H, d, J = 7 Hz, H-14); 1.00 (3H, s, H-15); 4.75 (2H, d, J
= 12, H-1′); 7.53 (1H, s, H-3′); 5.56 (2H, d, J = 3, H-1″); 7.40 (2H, m, H-3″ and H-5″); 7.30 (1H, m, H-4″).
13C-NMR (δ = ppm, 150M Hz): 41.3 (C-1); 34.9 (C-2); 66.3 (C-3); 84.4 (C-4); 44.2 (C-5); 40.7 (C-6); 37.8
(C-7); 79.8 (C-8); 36.3 (C-9); 30.0 (C-10); 139.8 (C-11); 169.7 (C-12); 122.7 (C-13); 16.6 (C-14); 18.7 (C-15);
63.8 (C-1′); 145.1 (C-2′); 122.7 (C-3′); 54.4 (C-1″); 134.2 (C-2″); 129.3 (C-3″); 128.2 (C-4″); 129.0 (C-5″).
HRMS-ES (m/z): [M + Na]+: Calcd. for C25H31N3O4Na: 460.2212; found 460.2217.
Compound 11: White amorphous solid, m.p.: 80–81 °C. [α]2D0: +7.3 (c 1.79; CHCl3). IR (KBr; υmax:
cm−1): 3433, 2962, 2924, 1757, 1456, 1261, 1092, 1120, 800. 1H-NMR (δ = ppm, 600M Hz): 1.37–1.42 (1H,
m, H-1); 1.71–1.77 (1H, m, H-2a); 2.01–2.04 (1H, m, H-2b); 3.96–4.00 (1H, m, H-3); 3.45 (1H, d, J = 7 Hz,
H-4); 1.68 (1H, dd, J = 15 Hz, H-6a); 1.71–1.77 (1H, m, H-6b); 3.03 (1H, m, H-7); 4.61–4.65 (1H, m, H-8);
1.71–1.77 (1H, m, H-9a); 2.13–2.18 (1H, m, H-9b); 1.95–1.98 (1H, m, H-10); 5.43 (1H, d, J = 2 Hz, H-13);
6.19 (1H, d, J = 2 Hz, H-13′); 1.01 (3H, d, J = 7 Hz, H-14); 0.99 (3H, s, H-15); 4.64–4.67 (2H, m, H-1′a) /
4.65–4.71 (2H, m, H-1′a); 4.47 (2H, d, J = 12, H-1′b) / 4.54 (2H, d, J = 12, H-1′b); 7.61 (2H, s, H-3′a); 7.58
(1H, s, H-3′b); 5.58 (d, J = 10, H-1″a); 5.54 (d, J = 10, H-1″b); 7.29–7.40 (10H, m, H-3″, H-4″ and H-5″).
13C-NMR (δ = ppm, 150M Hz): 41.0 (C-1); 33.2 (C-2); 73.9 (C-3); 83.6 (C-4); 44.3 (C-5); 40.3 (C-6); 37.8
(C-7); 79.8 (C-8); 36.3 (C-9); 30.1 (C-10); 139.7 (C-11); 169.8 (C-12); 122.9 (C-13); 16.7 (C-14); 18.5 (C-15);
62,3 (C-1′a); 63.2 (C-1′b); 145.2 (C-2′a); 145.3 (C-2′b); 123.1 (C-3′a); 123.4 (C-3′b); 54.5 (C-1″); 134.4
(C-2″); 128.3 (C-3″); 129.2 (C-4″); 129.0 (C-5″). HRMS-ES (m/z): [M + Na]+: Calcd. for C35H40N6O4Na:
631.3009; found 631.3015.
Compound 12: Amorphous solid, m.p.: 164–165 °C. [α]2D0: −76.3 (c 9.3; CHCl3). IR (KBr; υmax:
cm−1): 2927, 2854, 1767, 1734, 1709, 1657, 1466, 1238, 949. 1H-NMR (δ = ppm, 200M Hz): 3.02 (1H, dt, J
= 3 and 2 Hz, H-1); 7.65 (1H, dd, J = 2 and 6 Hz, H-2); 6.07 (1H, dd, J = 3 and 6 Hz, H-3); 5.38 (1H, br s,
H-6); 3.51 (1H, ddd, J = 8 and 12, H-7); 4.88 (1H, ddd, J = 2 and 7 Hz, H-8); 1.75 (1H, cd, J = 19 Hz,
H-9a); 2.43 (1H, m, H-9b); 2.07–2.18 (1H, m, H-10); 6.14 (1H, d, J = 3 Hz, H-13); 6.45 (1H, d, J = 3 Hz,
13
H-13′); 1.27 (3H, d, J = 7 Hz, H-14); 1.01 (3H, s, H-15); 2.00 (3H, brs, H-2′). C-NMR (δ = ppm, 50M
Hz): 53.2 (C-1); 162.1 (C-2); 129.7 (C-3); 208.9 (C-4); 55.4 (C-5); 77.6 (C-6); 47.7 (C-7); 78.1 (C-8); 40.2
(C-9); 26.1 (C-10); 137.4 (C-11); 169.7 (C-12); 125.0 (C-13); 20.0 (C-14); 18.4 (C-15); 169.5 (C-1′); 21.0
(C-2′). HRMS-ES (m/z): [M + Na]+: Calcd. for C17H20O5Na: 327.1208; found 327.1215.
Compound 13: Amorphous solid. m.p.: 82–84 °C. [α]2D0: −41.6 (c 11.2; CHCl3). IR (KBr; υmax: cm−1):
2960, 2929, 1761, 1714, 1464, 1246, 1109, 845. 1H-NMR (δ = ppm, 200M Hz): 3.20 (1H, dt, J = 6 and 12
Hz, H-1); 7.64 (1H, dd, J = 2 and 6 Hz, H-2); 5.99 (1H, dd, J = 3 and 6 Hz, H-3); 4.42 (1H, d, J = 2 Hz,
H-6); 3.30 (1H, m, H-7); 4.95 (1H, td, J = 3 and 8 Hz, H-8); 1.78 (1H, cd, J = 8 Hz, H-9a); 2.30 (1H, m,