Table 4. (Continued)

Mono-THF Acetogenins (Continued)

  1. 45. annoglacin A26(C37H69O7, MW624)

Position1217182122
1H (δ)3.60 m3.40 m3.80 m3.80 m3.80 m
13C (δ)71.8474.2883.1882.1571.54

White waxy solid. [α]D: +15.0° (CHCl₃). UV (λmax, MeOH, nm): 21.5 (log ε 3.62). IR (νmax, film, cm-1): 3413, 2920, 2850, 2280, 1742, 1657, 1630, 1551, 1528, 1467, 1321, 1075, 850, 791. MS: EIMS m/z 425, 407, 355, 337, 319, 301, 269, 251, 233, 141. NMR:1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): BST LC50 4.9 × 10-1, A-549 ED50 5.3 × 10-3, MCF-7 ED50 9.6 × 10-4, HT-29 ED50 5.3 × 10-3, A-498 ED50 9.0 × 10-1, PC-3 ED50 2.0 × 10-3, PAC-2 ED50 5.1 × 10-7. Source: Annona glabra, leaves.

  1. 46. annoglacin B26 (C37H69O7, MW624)

Position1217182122
1H ( \delta )3.60 m3.41 m3.80 m3.80 m3.41 m
13C ( \delta )71.8374.0082.5782.6474.08

White waxy solid. [α]D: +15.7° (CHCl_{3}). UV (λmax, MeOH, nm): 218 (log ε 3.48). IR (νmax, film, cm^{-1}): 3453, 2920, 2851, 1735, 1548, 1530, 1512, 1462, 1409, 1318, 1275, 1106, 1075, 1022, 965, 855, 673. MS: EIMS m/z 425, 407, 355, 337, 319, 301, 269, 251, 233, 141. NMR: 1H NMR (500MHz, CDCl_{3}), 13C NMR (125MHz, CDCl_{3}). Derivatives: per-MTPA esters (^{1}H NMR). Biological activities (μg/mL): BST LC_{50} 1.7 × 10^{-1}, A-549 ED_{50} 2.8 × 10^{-3}, MCF-7 ED_{50} 6.2 × 10^{-4}, HT-29 ED_{50} 5.3 × 10^{-3}, A-498 ED_{50} 4.0 × 10^{-1}, PC-3 ED_{50} 8.4 × 10^{-4}, PACA-2 ED_{50} 1.2 × 10^{-6}. Source: Annona glabra, leaves.

mosinone105 (reported as a cis and trans mixture) (C37H64O7, MW620)

  1. (2,4-cis)-mosinone
  2. (2,4-trans)-mosinone
  3. Position 9 15 16 19 20 23 24
  4. 1 H ( \delta ) -- 3.40 m 3.80 m 3.80 m 3.41 m 5.36 m 5.39 m
  5. 13 C ( \delta ) 210.80 73.49 82.63 82.63 73.91 128.92 130.78
  6. Position 9 15 16 19 20 23 24
  7. 1 H ( \delta ) -- 3.40 m 3.80 m 3.80 m 3.41 m 5.36 m 5.39 m
  8. 13 C ( \delta ) 210.80 73.49 82.63 82.63 73.91 128.92 130.78
  9. White waxy solid. [α]D: +4.8° (c 0.016, CH₂Cl₂). UV (λmax, MeOH, nm): 202 (log ε 2.96). MS: EIMS m/z 395, 377, 359, 323–307, 289, 225, 207. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀ 4.4 × 10⁻¹, A-549 ED₅₀ > 1, MCF-7 ED₅₀ > 1, HT-29 ED₅₀ > 1, A-498 ED₅₀ > 1, PC-3 ED₅₀ 3.2 × 10⁻², PACA-2 ED₅₀ 2.2 × 10⁻¹. Source: Annona squamosa, stem bark.
  10. mosin B*105 (C35H62O7, MW594)

Position915161920
1H (δ)--3.38 m3.81 m3.82 m3.87 m
13C (δ)211.3874.2183.1882.1471.51

White waxy solid. [α]D: +11.5° (c 0.005, CH₂Cl₂). UV (λmax, MeOH, nm): 222 (log ε 3.57). MS: EIMS m/z 325, 307, 289, 225, 207. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀ 2.9 × 10⁻¹, A-549 ED₅₀ 9.4 × 10⁻¹, MCF-7 ED₅₀ > 1, HT-29 ED₅₀ > 1, A-498 ED₅₀ > 1 × 10⁻¹, PC-3 ED₅₀ > 1, PACA-2 ED₅₀ 1.2 × 10⁻⁴. Source: Annona squamosa, stem bark.