530
Adjacent Bis-THF Acetogenins (Continued)
| Position | 15 | 16 | 19 | 20 | 23 | 24 | 28 | 29 |
|---|---|---|---|---|---|---|---|---|
| 1H ( \delta ) | 3.40 m | 3.86 m | 3.86 m | 3.93 m | 3.93 m | 3.86 m | 3.60 m | 3.60 m |
| 13C ( \delta ) | 74.2 | 83.4 | 82.9 | 82.6 | 82.2 | 71.5 | 74.6 | 74.7 |
White waxy solid. [α]D: +15.7° (c O62, CHCl_{3}). UV (λmax, MeOH, nm): 222 (log ε 3.54). IR (νmax, film, cm^{-1}): 3348, 2924, 1743, 1668, 1071. MS: EIMS (TMS) m/z 753, 663, 507, 489, 399, 367, 329, 173. NMR: 1H NMR (500 MHz, CDCl_{3}), 13C NMR (125 MHz, CDCl_{3}). Derivatives: formal acetal (1H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC50 4.3 × 10^{-1}, A-549 ED50 1.6, MCF-7 ED50 2.5 × 10^{-4}, HT-29 ED50 4.6 × 10^{-3}, A-498 ED50 1.5, PC-3 ED50 1.1, PAC-2 ED50 3.0. Source: Rollinia mucosa, leaves.
| Position | 10 | 12 | 15 | 16 | 19 | 20 |
|---|---|---|---|---|---|---|
| 1H (δ) | 3.82 m | 4.22 m | 3.97 m | 3.92 m | 3.83 m | 3.38 m |
| 13C (δ) | 71.7 | 80.5 | 80.9 | 81.0 | 82.8 | 74.4 |
Oil. UV (λmax, MeOH, nm): 222 (log ε 3.52). IR (νmax, film, cm-1): 3446, 2938. 1731, 1670, 1079. MS: EIMS m/z 395, 377, 365, 325, 307, 289, 269, 241, 223, 205, 199, 181, 141, 123. NMR:1H NMR (500MHz, CDCl3),13C NMR (125MHz, CDCl3). Derivatives: formal acetal (1H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC50 3.5, A-549ED50 4.6 × 10-2, MCF-7ED50 1.6 × 10-1, HT-29ED50 2.1, A-498ED50 1.6, PC-3ED50 2.5, PAC-2ED50 2.0. Source: Rollinia mucosa, leaves.
| Position | 10 | 11 | 14 | 15 | 18 | 23 | 24 |
|---|---|---|---|---|---|---|---|
| 1H (δ) | 3.42 m | 3.80 m | 3.80 m | 3.80 m | 3.80 m | 3.61 m | 3.61 m |
| 13C (δ) | 74.13 | 82.65 | 82.07 | 82.30 | 79.89 | 74.48 | 74.71 |
White wax solid. [α]D: -11.6° (c QOI3, CHCl3). UV (λmax, MeOH, nm): 220 (log ε 3.89). IR (νmax, film, cm-1): 3330, 2919, 2850, 1747, 1717, 1469, 1320, 1203, 1064, 956, 758 MS: EIMS m/z 467, 449, 431, 413, 397, 379, 361, 327, 311, 309, 293, 291, 275, 241, 223, 205, 171, 141. NMR:1H NMR (500MHz, CDCl3),13C NMR (125MHz, CDCl3). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): BST LC50 1.3 × 10-1, A-549 ED50 2.8 × 10-6, MCF-7 ED50 4.2 × 10-6, HT-29 ED50 5.7 × 10-6, A-498 ED50 1.0, PC-3 ED50 1.1, PAC-2 ED50 1.8. Source: Annona glabra, leaves.
| Position | 10 | 11 | 14 | 15 | 18 | 23 | 24 |
|---|---|---|---|---|---|---|---|
| 1H (δ) | 3.42 m | 3.80 m | 3.80 m | 3.80 m | 3.80 m | 3.43 m | 3.43 m |
| 13C (δ) | 74.18 | 82.78 | 82.60 | 81.80 | 79.31 | 74.05 | 74.35 |
White waxy solid. [α]D: +16.9° (c Q05, CHCl_{3}). UV (λmax, MeOH, nm): 223 (log ε 3.58). IR (νmax, film, cm^{-1}): 3382, 2926, 2854, 1748, 1540, 1456, 1318, 1270, 1199, 1072 MS: EIMS m/z 467, 449, 431, 413, 397, 379, 361, 327, 311, 309, 293, 291, 275, 241, 223, 205, 171, 141. NMR: 1H NMR (500 MHz, CDCl_{3}), 13C NMR (125 MHz, CDCl_{3}). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): BST LC50 3.1 × 10^{-1}, A-549 ED50 1.6 × 10^{-1}, MCF-7 ED50 1.8 × 10^{-3}, HT-29 ED50 1.9 × 10^{-2}, A-498 ED50 1.4, PC-3 ED50 1.2, PACA-2 ED50 2.8 × 10^{-1}. Source: Annona glabra. leaves.