Table 4. (Continued)
Adjacent Bis-THF Acetogenins (Continued)
mucoxin*9 (C37H67O7, MW622)
Position 89121314161
1H (δ) 3.42 m 3.95 m 4.31 m 3.71 m 4.32 m 4.04 m 3.53 m13C (δ) 73.6 83.4 78.9 83.5 72.8 79.9 73.7
Colorless oil. MS: E1MS m/z 337, 319, 269, 267, 251, 249, 197. NMR:1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3). Derivatives: per-MTPA esters (1H NMR), TMS (EIMS). Biological activities (μg/mL): A-549 ED50 3.6 × 10-2, MCF-7 ED50 3.7 × 10-3, HT-29 ED50 6.1 × 10-1, A-498 ED50 8.4 × 10-1, PC-3 ED50 3.1 × 10-1, PAC-2 ED50 3.3 × 10-1. Source: Rollinia mucosa leaves
Rollinia mucosa, leaves.
carolin A*28 (C37H66O7, MW622)
Position 15 16 19 20 23 24 281H (δ) 3.39 m 3.87 m 3.87 m 3.87 m 3.93 m 3.78 m 3.56 m13C (δ) 73.9 83.0 82.6 82.4 81.9 71.6 71.3
1H (δ) 3.39 m 3.87 m 3.87 m 3.87 m 3.93 m 3.78 m 3.56 m13C (δ) 73.9 83.0 82.6 82.4 81.9 71.6 71.3
Transparent oil. [α]D: +22circ (c 1, CHCl 3). UV (λmax, MeOH, nm): 208 (log ε 4.6). IR (νmax, film, cm-1): 3675, 3474, 1749, 1652, 1458. NMR: 1 H NMR (400 MHz, CDCl 3), 13 C NMR (50 MHz, CDCl 3). Derivatives: per-acetate (1 H NMR), formal acetal (1 H NMR). Biological activities (μg/mL): KB ED50 1 × 10-7, VERO KB ED50 2 × 10-3. Source: Annona spinescens, seeds.
77. carolin B*28 (C37H66O7, MW622)
| Position | 15 | 16 | 19 | 20 | 23 | 24 | 29 |
|---|
| 1H ( \delta ) | 3.35 m | 3.89 m | 3.89 m | 3.89 m | 3.90 m | 3.78 m | 3.55 m |
|---|
| 13C ( \delta ) | 73.9 | 83.0 | 82.6 | 82.4 | 81.9 | 71.5 | 71.3 |
|---|
Transparent oil. [α]D: +5° (c O.5, CHCl_{3}). UV (λmax, MeOH, nm): 208 (log ε 3.6). IR (νmax, film, cm^{-1}): 3677. 3575, 1753, 1619. NMR: 1H NMR (400 MHz, CDCl_{3}), 13C NMR (50 MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR). Biological activities (μg/mL): KB ED_{50} 5 × 10^{-6}, VERO ED_{50} 37 × 10^{-3}. Source: Annona spinescens, seeds.
78. carolin C28 (C35H62O7, MW594)
Transparent oil. [α]D: +8° (c O.5, CHCl_{3}). UV (λmax, MeOH, nm): 205 (log ε 4.0). IR (νmax, film, cm^{-1}): 3657, 2479, 1751, 1625. NMR: 1H NMR (400 MHz, CDCl_{3}), 13C NMR (50 MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR). Biological activities (μg/mL): KB ED_{50} 2 × 10^{-4}, VERO ED_{50} 5 × 10^{-2}. Source: Annona spinescens, seeds.
9-hydroxyasimicinone42 (reported as a cis and trans mixture) (C37H66O8, MW638)
79. (2,4-cis)-9-hydroxyasimicinone
| Position | 9 | 15 | 16 | 19 | 20 | 23 | 24 |
|---|
| 1H (δ) | 3.58 m | 3.39 m | 3.85 m | 3.85 m | 3.85 m | 3.85 m | 3.39 m |
|---|
| 13C (δ) | 71.64 | 74.05 | 83.06 | 81.79 | 81.76 | 83.16 | 73.96 |
|---|
527