Table 4. (Continued)
Adjacent Bis-THF Acetogenins (Continued)
| Position | 15 | 24 | 28 | 33 | 34 |
|---|---|---|---|---|---|
| 1H (δ) | 3.40 m | 3.85 m | 3.61 m | 3.83 m | 1.18 d |
| 13C (δ) | 74.20 | 71.54 | 71.54 | 67.92 | 22.02 |
White waxy solid. Mp: 63.5–65°C. [α]D: +124° (c O.23, MeOH). UV (λmax, MeOH, nm): 218 (log ε 4.07). IR (νmax, film, cm⁻¹): 3383, 2922, 1749, 1652, 1467, 1375, 1324, 1203, 1118, 1075, 949, 916, 871, 722 MS: EIMS m/z 537, 519, 509, 501, 491, 483, 473, 465, 447, 435, 429, 417, 399, 343, 325, 307, 295, 289, 277, 265, 203, 185, 173, 167, 155, 149, 137, 111, 101, 83, NMR: ¹H NMR (600 MHz, CDCl₃), ¹³C NMR (150 MHz, CDCl₃). Source: Uvaria microcarpa, seeds.
| Position | 13 | 14 | 17 | 18 | 21 | 22 |
|---|---|---|---|---|---|---|
| 1H (δ) | 3.81 m | 3.81 m | 3.85 m | 3.85 m | 3.90 m | 3.40 m |
| 13C (δ) | 73.97 | 83.02 | 81.11 | 80.99 | 83.02 | 71.87 |
White amorphous solid. [α]D: +17.5° (c O4, MeOH). UV (λmax, MeOH, nm): 210(log ε 3.95). IR (νmax, film, cm-1): 3430, 2924, 2849, 1750, 1647, 1462, 1316, 1200, 1070. MS: EIMS m/z 483, 465, 423, 353, 335, 317, 311, 293, 283, 265, 247, 241, 223, 153, 141, 123, 111. NMR: 1H NMR (400MHz, CDCl3), 13C NMR (100MHz, CDCl3). Derivatives: per-MTPA esters (1H NMR). Biological activities: NADH oxidase IC50 O.33 nM. Source: Rollinia membranacea. seeds.
| Position | 15 | 16 | 23 | 24 | 28 | 29 |
|---|---|---|---|---|---|---|
| 1H (δ) | 3.40 m | 3.83 m | 3.93 m | 3.86 m | 3.59 m | 3.59 m |
| 13C (δ) | 74.1 | 83.3 | 82.9 | 71.6 | 74.6 | 74.7 |
White wax. Mp: 35–39 °C. [α]D: +20° (c 1.3, MeOH). UV (λmax, MeOH, nm): 207 (log ε 3.89). IR (νmax, film, cm⁻¹): 3650, 3023, 2928, 1751, 1641, 1423, 1215, 1028, 930 MS: EIMS (TMS) m/z 753, 663, 573, 507, 489, 483, 437, 417, 399, 367, 347, 309, 173, 111, 83, 73. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: acetonide (¹H NMR), per-MTPA esters (¹H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC₅₀ 7.0 × 10⁻², A-549ED₅₀ 4.4 × 10⁻¹, MCF-7 ED₅₀ 9.2 × 10⁻¹, HT-29ED₅₀ < 10⁻⁷, A-498ED₅₀ 1.4, PC-3ED₅₀ 3.5 × 10⁻¹, PAC-2ED₅₀ 1.4. Source: Annona purpurea, seeds.
| Position | 10 | 15 | 16 | 23 | 24 | 29 |
|---|---|---|---|---|---|---|
| 1 H ( \delta ) | 3.58 m | 3.40 m | 3.83 m | 3.93 m | 3.85 m | 3.58 m |
| 13 C ( \delta ) | 71.8 | 74.0 | 83.2 | 82.8 | 71.5 | 71.8 |
Pale yellow wax. Mp: 36–38°C. [α]D: +27° (c 1.0, MeOH). UV (λmax, MeOH, nm): 208 (log ε =4.09). IR (νmax, film, cm⁻¹): 3100–3700, 3021, 2940, 2859, 1751, 1642, 1428, 1215, 1074, 927. MS: EIMS (TMS) m/z 765, 731, 675, 641, 595, 585, 551, 505, 495, 455, 461, 415, 365, 331, 297, 275, 241, 173, 151, 111, 107, 83, 73, NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: peracetate (¹H NMR), per-MTPA esters (¹H NMR), formal acetal (¹H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC₅₀ 2.9 × 10⁻², A-549 ED₅₀ 1.3, MCF-7 ED₅₀ 1.7, HT-29 ED₅₀ 3.2 × 10⁻¹, A-498 ED₅₀ 1.3, PC-3 ED₅₀ 1.1, PACA-2 ED₅₀ 2.0 Source: Annona purpurea, seeds.