Table 4. (Continued)
(2,4-cis)-trilobacinone Adjacent Bis-THF Acetogenins (Continued)
Position 15 16 19 20 23 24
1H ( \delta ) 3.37 ddd 3.83 m 3.97 ddd 4.04 ddd 3.83 m 3.39 ddd
13C ( \delta ) 74.5 83.2 81.7 80.8 82.6 74.0
(2,4-trans)-trilobacinone
Position 15 16 19 20 23 24
1H ( \delta ) 3.37 ddd 3.83 m 3.97 ddd 4.04 ddd 3.83 m 3.39 ddd
13C ( \delta ) 74.5 83.2 81.7 80.8 82.6 73.8
White wax. [α]D: +17.3° (c O.22, CHCl_{3}). IR (νmax, film, cm^{-1}): 3354, 2923, 2845, 1742, 1722, 1591, 1456, 1403, 1361, 1170, 1121, 1116, 1079 MS: EIMS (TMS) m/z 523, 453, 433, 383, 363, 313, 293, 243, 223. NMR: ^1H NMR (500MHz, CDCl_{3}), ^{13}C NMR (125 MHz, CDCl_{3}). Derivatives: per-MTPA esters (^{1}H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC_{50} 2.0 × 10^{-2}, A-549 ED_{50} 4.6 × 10^{-4}, MCF-7 ED_{50} 1.3 × 10^{-8}, HT-29 ED_{50} 1.6, A-498 ED_{50} 4.9 × 10^{-1}, PC-3 ED_{50} 2.8, PACA-2 ED_{50} 6.9 × 10^{-2}. Source: Asimina triloba, stem bark.
rollidecin C55(C35H62O6, MW578)
Position 12 15 16 19 20
1H (δ) 3.92 m 3.92 m 3.92 m 3.92 m 3.36 m
13C (δ) 80.1 80.7 81.5 82.5 74.7
White waxy solid. Mp: 42–43°C. UV (λmax, MeOH, nm): 222 (log ε 3.50). IR (νmax, film, cm⁻¹): 3345, 2936, 2859, 1741, 1674, 1071. MS: EIMS m/z 409, 379, 309, 291, 141, 123. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Biological activities (μg/mL): A-549 ED₅₀ 1.3, MCF-7 ED₅₀ 1.1, HT-29 ED₅₀ 6.3 × 10⁻², A-498 ED₅₀ 1.4, PC-3 ED₅₀ 2.9 × 10⁻¹, PACA-2 ED₅₀ 1.1 × 10⁻¹. Source: Rollinia mucosa, leaves.
88. rollidecin D^{55} (C_{37}H_{66}O_{6}, MW606)
Position 14 17 18 21 22
1H (δ) 3.92 m 3.92 m 3.92 m 3.92 m 3.36 m
13C (δ) 80.2 80.7 81.6 82.6 74.8
White waxy solid. Mp: 41–42°C. UV (λmax, MeOH, nm): 222 (log ε 3.5O). IR (νmax, film, cm⁻¹): 3345, 2936, 2859, 1741, 1674, 1071. MS: EIMS m/z 437, 407, 337, 319, 141, 123. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃), Biological activities (μg/mL): A-549ED₅₀.₅₉, MCF-7ED₅₀.₅O, HT-29ED₅₀.₅₄, A-498ED₅₀.₄O, PC-3ED₅₀.₁₉, PACA-2ED₅₀.₁O Source: Rollinia mucosa, leaves.
89. articulin30 (C37H66O8, MW638)
Position 12 15 16 19 20 23 24
| Position | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 |
|---|
| 1H (δ) | 3.59 m | 3.39 m | 3.84 m | 3.84 m | 3.84 m | 3.84 m | 3.84 m | 3.84 m | 3.84 m | 3.84 m | 3.84 m | 3.39 m |
|---|
| 13C (δ) | 71.67 | 74.04 | 83.17 | 81.74 | 81.85 | 82.84 | 74.15 | | | | | |
|---|
Solid. [α]D: +9.6° (c O 27, MeOH). IR (νmax, film, cm-1): 3450, 2920, 2840, 1750, 1600, 1450, 1300, 1060, 1020, 920 MS: EIMS m/z 467, 449, 397, 379, 369, 309, 269, 241, 171, 141. NMR: 1H NMR (200MHz, CDCl 3), 13C NMR (50MHz, CDCl 3). Derivatives: peracetate (1H NMR), TMS (EIMS). Biological activities (μg/mL): A-549ED50 6 × 10-3, MCF-7 ED50 4 × 10-3, HT-29ED50 6 × 10-1, RPMI-7951 ED50 10-3, U-251 ED50 10-2. Source: Annona crassiflora, seeds.
90. annonisin120 (C35H62O8, MW61O)
Position 8 13 14 17 18 21 22
1H (δ) 3.59 m 3.38 m 3.83 m 3.83 m 3.83 m 3.83 m 3.38 m
13C (δ) 71.4 74.1 83.2 81.8 81.8 83.2 74.1
White solid. [α]D: +30° (c O 2O, CHCl_{3}). UV (λmax, MeOH, nm): 209 (log ε 3.90). IR (νmax, film, cm^{-1}): 3432, 2923, 2850, 1748, 1436, 1372, 1068, 1032, 957, 753 MS: CIMS (methane) m/z 611, 593, 575, 557, 539, 521, 463, 439, 421, 403, 385, 369, 351, 333, 315, 311, 293, 281, 263, 245, 241, 223, 195, 171, 141, 123, 111. EIMS m/z 403, 385, 369, 333, 293, 281, 263, 241, 223, 141, 97. NMR: 1H NMR (200MHz, CDCl_{3}), 13C NMR (50MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR), TMS (EIMS). Source: Annona atemoya, seeds.
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