| Position | 4 | 10 | 15 | 16 | 19 | 20 | 34 |
|---|---|---|---|---|---|---|---|
| 1H (δ) | 5.04 m | 3.61 m | 3.42 m | 3.80 m | 3.80 m | 3.42 m | --- |
| 13C (δ) | 72.2 | 71.5 | 74.1 | 82.5 | 82.5 | 74.0 | 104.7 |
White amorphous powder. Mp: 92–94°C. [α]D: +17.4° (c O,O8, MeOH). IR (νmax, film, cm⁻¹): 3402, 2920, 2850, 1736. MS: EIMS m/z 455, 437, 419, 401, 385, 367, 349, 331, 299, 281, 269, 251, 199. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: phenylhydrazone (¹H NMR), per-MTPA esters (¹H NMR). Biological activities (μg/mL): KB IC₅₀ >10, HCT-8IC₅₀ >10, Bel IC₅₀ 7.1. Source: Goniothalamus donnaiensis, roots.
Position 12 15 16 19 20
1H (δ) 3.89 m 3.82 m 3.45 m 3.60 m 3.60 m13C (δ) 79.3 81.7 74.3 74.4 74.7
Solid. [α]D: +30° (c O.2, CHCl_{3}). UV (λmax, EtOH, nm): 209 (log ε 3.9). IR (νmax, film, cm^{-1}): 3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756 MS: EIMS m/z 379, 361, 343, 309, 291, 286, 269, 251. NMR: 1H NMR (400 MHz, CDCl_{3}), 13C NMR (50 MHz, CDCl_{3}). Source: Annona glauca, seeds.
Position 10 11 15 16 19 20
1H (δ) 3.60 m 3.60 m 3.45 m 3.79 m 3.79 m 3.43 m 13C (δ) 74.2 74.3 74.5 82.8 82.6 73.9
White solid. [α]D: +12.5° (c QO4, MeOH). UV (λmax, MeOH, nm): 218 (log ε 3.76). IR (νmax, film, cm-1): 3381, 2920, 2851, 1744, 1466. MS: EIMS m/z 377, 359, 353, 341, 335, 325, 317, 307, 289, 271, 269, 253, 251, 241, 223, 205, 199, 141, 123. NMR:1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3). Derivatives: acetonide (1H NMR). Biological activities (μg/mL): BST LC50 18.4, A-549 ED50 1.1 × 10-1, MCF-7 ED50 1.5 × 10-1, HT-29 ED50 6.7 × 10-1, A-498 ED50 1.4, PC-3 ED50 1.5 × 10-1, PAC-2 ED50 2.4 × 10-1. Source: Annona muricata, leaves.
Position 8 12 15 16 19 20
1H (δ) 3.61 m 3.66 m 3.45 m 3.79 m 3.79 m 3.40 m13C (δ) 71.3 71.3 74.3 82.8 82.3 74.2
White solid. [α]D: +8.0° (c 0.05, MeOH). UV (λmax, MeOH, nm): 220 (log ε 3.54). IR (νmax, film, cm-1): 3398, 2920, 2851, 1743, 1458. MS: EIMS m/z 377, 359, 343, 341, 325, 307, 289, 271, 269, 231, 213, 199, 195, 177, 141, 123. NMR: 1H NMR (500 MHz, CDCl 3), 13C NMR (125 MHz, CDCl 3). Derivatives: acetonide (1H NMR). Biological activities (μg/mL): BST LC50 1.8, A-549 ED50 1.9 × 10-1, MCF-7 ED50 1.9, HT-29 ED50 7.1 × 10-2, A-498 ED50 1.7, PC-3 ED50 4.5 × 10-1, PAC-2 ED50 5.0 × 10-2. Source: Annona muricata, leaves.
| Position | 10 | 13 | 14 | 15 | 17 | 18 |
|---|---|---|---|---|---|---|
| 1H ( \delta ) | 3.70 m | 3.62 m | 3.75 m | 4.38 m | 4.14 m | 3.47 m |
| 13C ( \delta ) | 72.0 | 71.5 | 89.0 | 73.6 | 81.2 | 73.8 |
White amorphous powder. Mp: 90–92°C. [α]D: +O (c O.25, MeOH). IR (νmax, film, cm⁻¹): 3429, 2920, 2850, 1746, 1469. MS: EIMS m/z 385, 367, 349, 331, 313, 299, 281, 263, 245, 241, 227, 141. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: peracetate (¹H NMR), formal acetal (¹H NMR), TMS (EIMS). Biological activities (μg/mL): KB IC₅₀ >10, HCT-8IC₅₀ >10, Bel IC₅₀ 6.7. Source: Goniothalamus donnaiensis, roots.