NATURAL PRODUCT RESEARCH
7
J ¼ 2.9 Hz, H-300), 3.49 (1H, dd, J ¼ 2.9, 9.6 Hz, H-400), 3.69 (1H, m, H-500), 3.84 (1H, m, H-
600a), 3.66 (1H, m, H-600b). 13C NMR data (150 MHz, in MeOH-d4): dC 70.6 (C-1), 28.8 (C-
2), 125.9 (C-3), 134.5 (C-4), 21.5 (C-5), 14.6 (C-6), 102.0 (C-10), 72.4 (C-20), 72.8 (C-30),
68.7 (C-40), 74.5 (C-50), 70.1 (C-60), 102.4 (C-100), 72.3 (C-200), 72.8 (C-300), 68.9 (C-400), 75.5
(C-500), 63.1 (C-600).
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Daturglycoside D (4): White amorphous powder. ½aꢂD -126 (c 0.1, MeOH). HR-ESI-MS:
1
m/z 403.1947 [M þ Na]þ (calcd for C17H32O9Na, m/z 403.1944). H NMR (400 MHz, in
MeOH-d4): dH 2.79 (1H, dd, J ¼ 6.7, 15.7 Hz, H-2a), 2.60 (1H, dd, J ¼ 5.6, 15.7 Hz, H-2b),
4.25 (1H, m, H-3), 1.76 (1H, m, H-4a), 1.67 (1H, m, H-4b), 3.75 (1H, m, H-5), 1.46 (2H, m,
H-6), 1.45 (1H, m, H-7a), 1.33 (1H, m, H-7b), 1.33 (2H, m, H-8), 1.34 (2H, m, H-9), 0.92
(3H, t, J ¼ 6.9 Hz, H-10), 4.71 (1H, d, J ¼ 8.0 Hz, H-10), 3.23 (1H, dd, J ¼ 3.0, 8.0 Hz, H-20),
4.02 (1H, t, J ¼ 3.0 Hz, H-30), 3.45 (1H, dd, J ¼ 3.0, 9.6 Hz, H-40), 3.66 (1H, m, H-50), 3.80
(1H, dd, J ¼ 1.8, 11.3 Hz, H-60a), 3.63 (1H, dd, J ¼ 5.8, 11.3 Hz, H-60b), 3.68 (3H, s, 1-
OMe). 13C NMR data (100 MHz, in MeOH-d4): dC 174.0 (C-1), 42.1 (C-2), 77.9 (C-3), 43.3
(C-4), 70.7 (C-5), 38.8 (C-6), 26.3 (C-7), 33.1 (C-8), 23.7 (C-9), 14.4 (C-10), 102.0 (C-10),
72.4 (C-20), 72.9 (C-30), 68.9 (C-40), 75.3 (C-50), 63.3 (C-60), 52.1 (1-OMe).
20
Daturglycoside E (5): White amorphous powder. ½aꢂD -26 (c 0.1, MeOH). HR-ESI-MS:
1
m/z 401.1787 [M þ Na]þ (calcd for C17H30O9Na, m/z 401.1788). H NMR (400 MHz, in
MeOH-d4): dH 2.78 (1H, dd, J ¼ 6.7, 15.6 Hz, H-2a), 2.58 (1H, dd, J ¼ 5.6, 15.6 Hz, H-2b),
4.24 (1H, m, H-3), 1.70 (2H, m, H-4), 3.81 (1H, m, H-5), 2.23 (2H, t, J ¼ 6.4 Hz, H-6), 5.40
(1H, m, H-7), 5.47 (1H, m, H-8), 2.07 (2H, m, H-9), 0.97 (3H, t, J ¼ 7.5 Hz, H-10), 4.72 (1H,
d, J ¼ 8.0 Hz, H-10), 3.24 (1H, dd, J ¼ 3.0, 8.0 Hz, H-20), 4.03 (1H, t, J ¼ 3.0 Hz, H-30), 3.45
(1H, dd, J ¼ 3.0, 9.6 Hz, H-40), 3.62 (1H, m, H-50), 3.79 (1H, m, H-6’a), 3.63 (1H, m, H-6’b),
3.67 (3H, s, 1-OMe). 13C NMR data (100 MHz, in MeOH-d4): dC 174.0 (C-1), 42.2 (C-2),
77.9 (C-3), 42.6 (C-4), 70.7 (C-5), 36.4 (C-6), 125.8 (C-7), 134.7 (C-8), 21.7 (C-9), 14.4 (C-
10), 102.1 (C-10), 72.4 (C-20), 72.9 (C-30), 68.9 (C-40), 75.3 (C-50), 63.3 (C-60), 52.1 (1-OMe).
20
Daturglycoside F (6): White amorphous powder. ½aꢂD -34 (c 0.1, MeOH). HR-ESI-MS:
1
m/z 409.1840 [M þ Na-H2O]þ (calcd for C19H32O9Na, m/z 409.1838). H NMR (400 MHz,
in MeOH-d4): dH 1.75 (1H, m, H-2a), 1.41 (1H, dd, J ¼ 10.2, 13.0 Hz, H-2b), 3.91 (1H, m,
H-3), 2.42 (1H, ddd, J ¼ 1.3, 5.0, 14.6 Hz, H-4a), 1.80 (1H, dd, J ¼ 8.4, 14.6 Hz, H-4b), 7.17
(1H, d, J ¼ 15.8 Hz, H-7), 6.19 (1H, d, J ¼ 15.8 Hz, H-8), 2.29 (3H, s, Me-10), 0.97 (3H, s,
Me-11), 1.21 (3H, s, Me-12); 1.19 (3H, s, Me-10), 4.69 (1H, d, J ¼ 8.0 Hz, H-10), 3.24 (1H,
dd, J ¼ 3.0, 8.0 Hz, H-20), 4.04 (1H, t, J ¼ 3.0 Hz, H-30), 3.49 (1H, dd, J ¼ 3.0, 9.7 Hz, H-40),
3.68 (1H, m, H-50), 3.84 (1H, m, H-60a), 3.66 (1H, m, H-60b). 13C NMR data (100 MHz, in
MeOH-d4): dC 36.0 (C-1), 45.3 (C-2), 72.6 (C-3), 38.3 (C-4), 68.4 (C-5), 71.1 (C-6), 145.3 (C-
7), 133.8 (C-8), 200.3 (C-9), 27.5 (C-10), 25.5 (C-11), 29.5 (C-12), 20.2 (C-13), 100.4 (C-10),
72.3 (C-20), 73.0 (C-30), 68.9 (C-40), 75.4 (C-50), 63.1 (C-60).
20
Daturglycoside G (7): White amorphous powder. ½aꢂD -64 (c 0.1, MeOH). HR-ESI-MS: m/z
1
377.0849 [M þ Na]þ (calcd for C16H18O9Na, m/z 377.0849). H NMR (400 MHz, in MeOH-d4):
dH 6.31 (1H, d, J¼ 9.5 Hz, H-3), 7.90 (1H, d, J¼ 9.5Hz, H-4), 7.21 (1H, s, H-5), 7.17 (1H, s, H-
8), 5.39 (1H, d, J¼ 7.9 Hz, H-10), 3.69 (1H, m, H-20), 4.16 (1H, t, J¼ 2.8 Hz, H-30), 3.62 (1H, dd,
J¼ 2.8, 9.7 Hz, H-40), 3.93 (1H, m, H-50), 3.89 (1H, m, H-60a), 3.70 (1H, m, H-60b), 3.91 (3H, s,
7-OMe). 13C NMR data (100 MHz, in MeOH-d4): dC 163.6 (C-2), 114.5 (C-3), 145.7 (C-4), 110.8
(C-5), 152.1 (C-6), 148.3 (C-7), 105.1 (C-8), 150.7 (C-9), 114.4 (C-10), 100.2 (C-10), 71.9 (C-20),
73.0 (C-30), 68.5 (C-40), 76.0 (C-50), 62.7 (C-60), 57.1 (7-OMe).