Journal of Natural Products
Article
= 2.8 Hz, H-12), 5.26 (1H, s, H-22), 4.90 (1H, brt, H-15), 4.86 (1H, d,
J = 5.6 Hz, H-1), 3.48 (1H, dd, J = 5.6, 3.7 Hz, H-2), 3.36 (1H, m, H-
3), 3.02 (1H, t, J = 11.3 Hz, H-9), 2.91 (1H, dd, J = 11.2, 4.9 Hz, H-5),
2.55 (1H, m, H-14), 2.53 (1H, m, H-16), 2.40 (1H, m, H-8), 2.31
(1H, m, H-20), 2.25 (3H, s, OCOCH3-1), 2.20 (3H, s, OCOCH3-12),
2.12 (2H, m, H-4), 2.11 (1H, m, H-17), 2.05 (3H, s, OCOCH3-11),
2.00 (3H, s, H-27), 1.74 (3H, s, H-28), 1.18 (3H, s, H-18), 1.02 (3H,
d, J = 6.9 Hz, H-21), 0.84 (3H, s, H-19); 13C NMR (125 MHz,
CDCl3) δ 202.0 (C-6), 182.1−181.1 (4C, C-12′, C-5′, C-12″, and C-
5″), C-26 (n.d.), 170.7 (11-OCOCH3), 169.6 (1-OCOCH3), 169.4
(12−OCOCH3), 162.9 (2C, C-1′ and C-1″), 153.1 (C-23), 135.7−
132.0 (16C, C-13′, C-13″, C-15′, C-15″, C-4′, C-4″, C-8′, C-8″, C-9′,
C-9″, C-2′, C-2″, C-6′, C-6″, C-11′, and C-11″), 128.0−126.9 (8C, C-
3′, C-3″, C-7′, C-7″, C-10′, C-10″, C-14′, and C-14″), 116.5 (C-25),
113.0 (C-22), 79.0 (C-7), 73.8 (C-12), 72.8 (C-1), 71.4 (C-11), 70.5
(C-15), 57.1 (C-14), 53.4 (C-16), 52.3 (C-3), 52.3 (C-24), 49.6 (C-2),
48.0 (C-17), 43.6 (C-13), 42.7 (C-5), 42.7 (C-10), 41.6 (C-9), 39.3
(C-8), 31.2 (C-20), 25.9 (C-28), 21.3 (C-4), 21.3 (OCOCH3-12),
21.0 (OCOCH3-11), 20.8 (OCOCH3-1), 20.2 (C-21), 13.9 (C-18),
13.0 (C-19), 2.0 (C-27); HRMS m/z 1151.3316 [M + Na]+ (calcd for
C64H56O19Na, 1151.3308).
(3H, s, OCOCH3-1), 2.14 (3H, s, OCOCH3-12), 2.09 (1H, m, H-3′),
2.02 (1H, m, H-16), 2.01 (1H, m, H-4b), 1.99 (3H, s, OCOCH3-11),
1.74 (3H, s, H-27), 1.71 (1H, m, H-8), 1.33 (3H, s, H-28), 1.02 (3H,
d, J = 6.9 Hz, H-21), 0.93 (6H, d, J = 7.0 Hz, H-4′ and H-5′), 0.88
(3H, s, H-18), 0.76 (3H, s, H-19); 13C NMR (125 MHz, CDCl3) δ
209.5 (C-6), 176.7 (C-26), 173.2 (C-1′), 170.6 (11-OCOCH3), 169.2
(1-OCOCH3), 169.0 (12-OCOCH3), 92.2 (C-23), 79.1 (C-25), 74.9
(C-7), 73.6 (C-12), 72.6 (C-1), 71.0 (C-15), 70.8 (C-11), 65.6 (C-
22), 54.3 (C-14), 52.2 (C-3), 49.7 (C-2), 47.8 (C-16), 47.2 (C-24),
44.0 (C-10), 43.6 (C-17), 43.4 (C-3′), 43.2 (C-8), 43.1 (C-13), 42.2
(C-5), 40.4 (C-9), 31.7 (C-20), 23.7 (C-27), 24.3 (C-2′), 22.6 (C-4′
and C-5′), 21.3 (C-4), 21.2 (OCOCH3-11), 20.8 (OCOCH3-12), 20.3
(OCOCH3-1), 18.7 (C-21), 19.4 (C-28), 13.1 (C-19), 13.4 (C-19);
HRMS m/z 761.3416 [M + H]+ (calcd for C39H53O15, 761.3384).
Compound 22: white powder; 1H NMR (500 MHz, CDCl3) δ 5.52
(1H, t, J = 9.1 Hz, H-15), 5.26 (1H, dd, J = 11.8, 2.8 Hz, H-11), 5.18
(1H, d, J = 2.8 Hz, H-12), 4.72 (1H, d, J = 5.5 Hz, H-1), 3.94 (1H, dd,
J = 10.2 Hz, H-7), 3.78 (1H, brd, OH-7), 3.46 (1H, t, J = 5.4, H-2),
3.37 (1H, m, H-3), 3.26 (1H, s, H-22), 2.76 (1H, m, H-5), 2.67 (1H,
m, H-9), 2.40 (1H, dd, J = 9.0, 9.0 Hz, H-14), 2.25 (2H, m, H-4), 2.17
(3H, s, OCOCH3-1), 2.14 (3H, s, OCOCH3-12), 2.07 (1H, m, H-16),
2.04 (1H, m, H-17), 1.98 (3H, s, OCOCH3-11), 1.73 (3H, s, H-27),
1.68 (1H, m, H-8), 1.60 (1H, m, H-20), 1.32 (3H, s, H-28), 1.01 (3H,
s, H-3′), 0.99 (3H, d, J = 7.7 Hz, H-21), 0.92 (3H, s, H-4′), 0.91 (3H,
s, H-5′), 0.87 (3H, s, H-18), 0.76 (3H, s, H-19); 13C NMR (125 MHz,
CDCl3) δ 209.5 (C-6), 177.6 (C-26), 173.1 (C-1′), 170.8 (12-
OCOCH3), 169.8 (11-OCOCH3), 169.1 (1-OCOCH3), 91.5 (C-23),
79.1 (C-25), 74.9 (C-7), 73.8 (C-12), 72.8 (C-1), 70.9 (C-15), 70.7
(C-11), 65.7 (C-22), 54.1 (C-14), 52.0 (C-3), 49.8 (C-2), 47.7 (C-
16), 46.8 (C-24), 44.7 (C-17), 44.3 (C-13), 43.9 (C-2′), 43.3 (C-10),
42.4 (C-8), 40.2 (C-9), 40.1 (C-5), 31.7 (C-20), 23.7 (C-27), 22.8 (C-
3′−C-5′), 21.4 (C-4), 21.2 (OCOCH3-11), 20.9 (OCOCH3-1/12),
20.7 (OCOCH3-1/12), 19.7 (C-28), 18.7 (C-21), 13.4 (C-18), 12.6
(C-19); HRMS m/z 761.3371 [M + H]+ (calcd for C39H53O15,
761.3384).
Compound 19: white powder; 1H NMR (500 MHz, CDCl3) δ 5.60
(1H, t, J = 9.0 Hz, H-15), 5.30 (1H, dd, J = 10.1, 2.5 Hz, H-11), 5.28
(1H, d, J = 2.7, H-12), 4.76 (1H, d, J = 5.0 Hz, H-1), 4.02 (1H, dd, J =
10.2, 3.2 Hz, H-7), 3.75 (1H, d, J = 3.2, OH-7), 3.49 (1H, t, J = 3.8 Hz,
H-2), 3.40 (1H, m, H-3), 3.28 (1H, s, H-22), 2.79 (1H, m, H-5), 2.76
(1H, m, H-9), 2.48 (1H, m, H-14), 2.09 (1H, m, H-16), 2.25 (2H, m,
H-4), 2.20 (3H, s, OCOCH3-1), 2.16 (3H, s, OCOCH3-12), 2.01 (3H,
s, OCOCH3-11), 2.12 (1H, dd, J = 13.8, 10.5, H-17), 1.81 (3H, s, H-
27), 1.75 (1H, m, H-8), 1.62 (1H, m, H-20), 1.58 (1H, m, H-2′), 1.34
(3H, s, H-28), 1.05 (3H, d, J = 6.95 Hz, H-21), 0.96 (2H, m, H-3′/H-
4′), 0.90 (3H, s, H-18), 0.79 (3H, s, H-19), 0.76 (2H, m, H-3′/H-4′);
13C NMR (125 MHz, CDCl3) δ 210.2 (C-6), 177.6 (C-26), 174.9 (C-
1′), 171.9 (11-OCOCH3), 169.6 (1-OCOCH3), 169.3 (12-
OCOCH3), 91.9 (C-23), 78.7 (C-25), 75.3 (C-7), 73.9 (C-12), 72.8
(C-1), 71.5 (C-15), 71.2 (C-11), 65.9 (C-22), 54.2 (C-14), 52.3 (C-3),
49.9 (C-2), 48.0 (C-16), 46.1 (C-24), 45.0 (C-17), 43.8 (C-13), 43.1
(C-8), 42.9 (C-10), 42.2 (C-5), 40.5 (C-9), 32.1 (C-20), 24.0 (C-27),
21.5 (C-4), 21.1 (OCOCH3-1 and OCOCH3-11), 20.4 (OCOCH3-
12), 19.9 (C-28), 18.6 (C-21), 14.3 (C-2′), 13.5 (C-18), 13.1 (C-19),
8.6 (C-3′ and C-4′); HRMS m/z 745.3063 [M + H]+ (calcd for
C38H49O15, 745.3071).
Compound 23: white powder; 1H NMR (600 MHz, CDCl3) δ 7.95
(1H, s, H-1′), 5.60 (1H, brt, H-11), 5.32 (1H, dd, J = 11.0, 2.3 Hz, H-
11), 5.20 (1H, d, J = 2.3, Hz, H-12), 4.71 (1H, d, J = 5.5 Hz, H-1),
4.02 (1H, dd, J = 10.4, 3.8 Hz, H-7), 3.89 (1H, s, OH-7), 3.46 (1H, t, J
= 4.8, H-2), 3.37 (1H, m, H-3), 3.27 (1H, s, H-22), 2.73 (1H, m, H-5),
2.70 (1H, m, H-9), 2.49 (1H, t, J = 10.1 Hz, H-14), 2.20 (2H, m, H-4),
2.16 (3H, s, OCOCH3-1), 2.13 (3H, s, OCOCH3-12), 2.11 (1H, dd, J
= 13.3, 10.0 Hz, H-16), 2.08 (1H, dd, J = 13.1, 8.8 Hz, H-17), 1.98
(3H, s, OCOCH3-11), 1.73 (1H, m, H-8), 1.76 (3H, s, H-27), 1.65
(1H, m, H-20), 1.30 (3H, s, H-28), 1.03 (3H, d, J = 7.4 Hz, H-21),
0.88 (3H, s, H-18), 0.77 (3H, s, H-19); 13C NMR (150 MHz, CDCl3)
δ 209.3 (C-6), 176.9 (C-26), 170.5 (11−OCOCH3), 169.4 (1−
OCOCH3), 169.1 (12−OCOCH3), 92.4 (C-23), 79.1 (C-25), 74.7
(C-7), 73.8 (C-12), 72.6 (C-1), 70.8 (C-11), 70.4 (C-15), 65.8 (C-
22), 53.8 (C-14), 52.2 (C-3), 49.7 (C-2), 47.9 (C-16), 46.8 (C-24),
45.3 (C-17), 44.0 (C-13), 43.3 (C-10), 42.9 (C-8), 42.2 (C-9), 40.1
(C-5), 31.8 (C-20), 23.9 (C-27), 21.4 (C-4), 21.2 (OCOCH3-11),
20.5 (OCOCH3-12), 20.2 (OCOCH3-1), 19.5 (C-28), 18.8 (C-21),
13.2 (C-18), 13.0 (C-19); HRMS m/z 705.2750 [M + H]+ (calcd for
C35H45O15, 705.2758).
Compound 20: white powder; 1H NMR (500 MHz, CDCl3) δ 5.58
(1H t, J = 9.1 Hz,, H-15), 5.29 (1H, dd, J = 11.0, 1.7 Hz, H-11), 5.20
(1H, d, J = 1.7, H-12), 4.71 (1H, d, J = 5.5 Hz, H-1), 3.91 (1H, dd, J =
10.3, 3.6 Hz, H-7), 3.75 (1H, d, J = 3.6 Hz, OH-7), 3.46 (1H, t, J = 5.0,
H-2), 3.36 (1H, m, H-3), 3.25 (1H, s, H-22), 2.76 (1H, m, H-5), 2.67
(1H, m, H-9), 2.60 (1H, m, H-2′), 2.40 (1H, t, J = 9.1 Hz, H-14), 2.23
(2H, m, H-4), 2.18 (3H, s, OCOCH3-1), 2.15 (3H, s, OCOCH3-12),
2.08 (1H, m, H-16), 2.02 (1H, m, H-17), 1.99 (3H, s, OCOCH3-11),
1.69 (1H, m, H-8), 1.64 (1H, m, H-20), 1.73 (3H, s, H-27), 1.32 (3H,
s, H-28), 1.14 (3H, d, J = 7.0 Hz, H-3′), 1.12 (3H, d, J = 7.0 Hz, H-4′),
1.01 (3H, d, J = 7.7 Hz, H-21), 0.88 (3H, s, H-18), 0.76 (3H, s, H-19);
13C NMR (125 MHz, CDCl3) δ 209.4 (C-6), 177.7 (C-26), 176.8 (C-
1′), 170.0 (12−OCOCH3), 169.9 (11−OCOCH3), 169.5 (1−
OCOCH3), 92.1 (C-23), 78.6 (C-25), 75.1 (C-7), 73.8 (C-12), 72.8
(C-1), 71.4 (C-15), 70.8 (C-11), 65.6 (C-22), 54.2 (C-14), 52.0 (C-3),
49.8 (C-2), 47.8 (C-16), 46.9 (C-24), 44.7 (C-17), 44.3 (C-13), 43.1
(C-10), 42.7 (C-8), 42.5 (C-5), 40.2 (C-9), 34.7 (C-2′), 31.7 (C-20),
23.7 (C-27), 21.4 (C-4), 21.2 (OCOCH3-11), 20.9 (OCOCH3-1),
20.7 (OCOCH3-12), 19.8 (C-28), 18.9 (C-3′ and C-4′), 18.5 (C-21),
13.4 (C-18), 12.9 (C-19); HRMS m/z 747.3197 [M + H]+ (calcd for
C38H51O15, 747.3227).
1
Compound 24: pale yellow powder; H NMR (400 MHz, CDCl3)
δ 8.84 (1H, d, J = 1.6 Hz, H-3′), 8.44 (1H, dd, J = 8.2, 1.6 Hz, H-15′),
8.36 (1H, d, J = 8.1 Hz, H-14′), 8.33 (2H, m, H-7′ and H-10′), 7.85
(2H, m, H-8′ and H-9′), 5.83 (1H, t, J = 9.3 Hz, H-15), 5.32 (1H, dd, J
= 11.5, 2.8 Hz, H-11), 5.26 (1H, d, J = 2.7 Hz, H-12), 4.71 (1H, d, J =
5.5 Hz, H-1), 3.82 (1H, d, J = 10.6 Hz, H-7), 3.46 (1H, dd, J = 5.5, 3.7
Hz, H-2), 3.32 (1H, m, H-3), 3.30 (1H, s, H-22), 2.77 (1H, t, J = 11.4
Hz, H-9), 2.70 (1H, dd, J = 10.8, 5.2 Hz, H-5), 2.60 (1H, t, J = 10.2
Hz, H-14), 2.30 (3H, s, OCOCH3-1), 2.30 (3H, s, OCOCH3-12), 2.26
(1H, dd, J = 13.4, 9.8 Hz, H-16), 2.15 (1H, m, H-17), 2.10 (2H, m, H-
4), 2.01 (3H, s, OCOCH3-11), 1.84 (3H, s, H-27), 1.73 (1H, m, H-8),
1.63 1H, (m, H-20), 1.38 (3H, s, H-28), 1.07 (3H, d, J = 7.4 Hz, H-
21), 0.96 (3H, s, H-18), 0.75 (3H, s, H-19); 13C NMR (100 MHz,
CDCl3) δ 209.2 (C-6), 183.4 (C-5′), 182.6 (C-12′), 177.1 (C-26),
170.9 (11-OCOCH3), 169.9 (1-OCOCH3), 169.5 (12-OCOCH3),
Compound 21: white powder; 1H NMR (500 MHz, CDCl3) δ 5.55
(1H, t, J = 9.0 Hz, H-15), 5.27 (1H, dd, J = 11.8, 2.6 Hz, H-11), 5.17
(1H, d, J = 2.6 Hz, H-12), 4.73 (1H, d, J = 5.5 Hz, H-1), 3.97 (1H, dd,
J = 10.2, 3.3 Hz, H-7), 3.77 (1H, d, J = 3.3 Hz, OH-7), 3.47 (1H, t, J =
5.0, H-2), 3.37 (1H, m, H-3), 3.25 (1H, s, H-22), 2.76 (1H, m, H-5),
2.70 (1H, m, H-9), 2.44 (1H, t, J = 9.8 Hz, H-14), 2.32 (2H, m, H-2′),
2.29 (1H, m, H-17), 2.20 (1H, m, H-4a), 2.02 (1H, m, H-20), 2.17
L
J. Nat. Prod. XXXX, XXX, XXX−XXX