Table 4. (Continued)
Mono-THF Acetogenins (Continued)
65. annopentocin B116 (C35H64O8, MW612)
Position 10 12 15 16 19 20
1H (δ) 3.80 m 4.18 m 3.90 m 3.47 m 3.41 m 3.41 m
13C (δ) 71.6 80.0 82.4 73.9 74.3 74.6
White oil. [α]D: +15° (c 1O, CHCl₃). UV (λmax, MeOH, nm): 214 (ε 9800). IR (νmax, film, cm⁻¹): 3400, 2935, 2845, 1749, 1465. MS: EIMS (TMS) m/z 701, 611, 521, 503, 469, 431, 413, 385, 379, 341, 323, 295, 289, 271, 213, 181. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: acetonide (¹H NMR), per-MTPA esters (¹H NMR), peracetate (¹H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC₅₀ 1.1 × 10¹, A-549 ED₅₀ 2.7 × 10⁻², MCF-7 ED₅₀ 3.6, HT-29 ED₅₀ 1.6, A-498 ED₅₀ 3.8 × 10⁻¹, PC-3 ED₅₀ 2.1 × 10⁻¹, PACA-2 ED₅₀ 1.6 × 10⁻¹. Source: Annona muricata, leaves.
66. annopentocin C116 (C35H64O8, MW61)
| Position | 10 | 12 | 15 | 16 | 19 | 20 |
|---|
| 1H (δ) | 3.80 m | 4.18 m | 3.92 m | 3.48 m | 3.58 m | 3.62 m |
|---|
| 13C (δ) | 71.7 | 80.0 | 82.4 | 73.8 | 74.6 | 74.8 |
|---|
White oil. [α]D: +9° (c 11, CHCl₃). UV (λmax, MeOH, nm): 214 (ε 9750). IR (νmax, film, cm⁻¹): 3410, 2930, 2835, 1741, 1455. MS: EIMS (TMS) m/z 701, 611, 521, 503, 469, 431, 413, 385, 379, 341, 323, 295, 289, 271, 213, 181. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: acetonide (¹H NMR), per-MTPA esters (¹H NMR), peracetate (¹H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC₅₀ 1.4 × 10¹, A-549 ED₅₀ 21 × 10⁻², MCF-7 ED₅₀ 3.0 × 10⁻¹, HT-29 ED₅₀ 1.2, A-498 ED₅₀ 2.6 × 10⁻¹, PC-3 ED₅₀ 2.3 × 10⁻¹, PAC-2 ED₅₀ 4.3 × 10⁻¹.
annomuricin-D-one116 (reported as a cis and trans mixture) (C35H64O8, MW612)
(2,4-cis)-annomuricin-D-one
Position 10 11 15 16 19 20
1H (δ) 3.45 m 3.45 m 3.41 m 3.80 m 3.80 m 3.41 m
13C (δ) 73.9 74.3 74.4 82.25 82.7 74.5
(2,4-trans)-annomuricin-D-one
Position 10 11 15 16 19 20
1H (δ) 3.45 m 3.45 m 3.41 m 3.80 m 3.80 m 3.41 m
13C (δ) 73.9 74.3 74.4 82.5 82.7 74.5
White powder. [α]D: +15° (c 1Q, CHCl_{3}). UV (λmax, MeOH, nm): 205 (ε 7750). IR (νmax, film, cm^{-1}): 3425, 2925, 2835, 1765, 1715, 1455, 1367. MS: EIMS (TMS) m/z 629,587, 559, 539,497, 469, 449, 407, 379, 359, 341, 317, 313, 289, 271, 251, 223, 181. NMR: 1H NMR (500MHz, CDCl_{3}), {}^{13}C NMR (125 MHz, CDCl_{3}). Derivatives: per-MTPA esters (^{1}H NMR), formal acetal (^{1}H NMR), TMS (EIMS). Biological activities: BST LC_{50} 4.8, A-549 ED_{50}<1O^{-2}, MCF-7 ED_{50} 6.1 \times 10^{-1}, HT-29 ED_{50}<1O^{-2}, A-498 ED_{50} 1.2 \times 10^{-1}, PC-3 ED_{50} 1.3, PACA-2 ED_{50}<1O^{-2}. Source: Annona muricata, leaves
uvaribonone*134 (C39H68O8 MW664)
| Position | 5 | 15 | 17 | 18 | 21 | 22 |
|---|
| 1H (δ) | - | 3.42 m | 5.10 m | 3.83 m | 3.83 m | 3.39 m |
|---|
| 13C (δ) | 209.3 | 70.1 | 71.7 | 82.8 | 82.9 | 74.1 |
|---|
Wäxy solid. Mp: 42–44 °C. [α]D: +15° (c O.O.G, CHCl_{3}). IR (νmax, film, cm^{-1}): 3470, 2925, 2825, 1755, 1740, 1720, 1661. MS: EIMS (TMS) m/z 604, 586, 568, 465, 405, 395, 387, 335, 317, 309, 291, 269, 251, 199, 181, 153, 125. NMR: ^{1}H NMR (500 MHz, CDCl_{3}), ^{13}C NMR (125 MHz, CDCl_{3}). Derivatives: TMS (EIMS). Source: Uvaria boniana, bark.
525