Table 4. (Continued)

Mono-THF Acetogenins (Continued)

10. 10. goniotrionin10 (C35H62O6, MW578)

Whitish wax. UV (λmax, MeOH, nm): 218 (log ε 3.46). IR (νmax, film, cm-1): 3368, 2916, 2849, 1740, 1721, 1467, 1328, 1086, 1058, 841 MS: EIMS m/z 297, 281, 263, 253, 245, 239, 221, 203. NMR:1H NMR (500 MHz, CDCl 3),13C NMR (125 MHz, CDCl 3). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): A-549 ED50 7.7 × 10-3, MCF-7 ED50 5.3 × 10-6, HT-29 ED50 3.4 × 10-1, A-498 ED50 2.0 × 10-3, PC-3 ED50 3.6 × 10-1, PAC-2 ED50 5.4 × 10-3. Source: Goniothalamus giganteus, stem bark.

squamoxine B*42 (reported as a cis and trans mixture) (C37H68O7, MW630)

11. (2,4-cis)-squamoxine B
12. Position 11 17 18 21 22
13. 1H (δ) 3.58 m 3.39 m 3.82 m 3.87 m 3.82 m
14. 13C (δ) 71.84 74.28 83.18 82.14 71.52
15. Position 11 17 18 21 22
16. 1H (δ) 3.58 m 3.39 m 3.82 m 3.87 m 3.82 m
17. 13C (δ) 71.84 74.28 83.18 82.14 71.52
12. (2,4-trans)-squamoxine B

White amorphous powder. [α]D: +23.6° (c 0.20, CH₂Cl₂). UV (λmax, MeOH, nm): 203 (log ε 2.85). IR (νmax, film, cm⁻¹): 3444, 2916, 1770, 1715, 1470. MS: EIMS m/z 425, 389, 337, 319, 301, 255. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀ 4.6 × 10⁻², A-549 ED₅₀ 3.8 × 10⁻³, MCF-7 ED₅₀ 1.4 × 10⁻³, HT-29 ED₅₀ 2.7 × 10⁻³, A-498 ED₅₀ 4.0 × 10⁻³, PC-3 ED₅₀ 5.0 × 10⁻², PACA-2 ED₅₀ 8.3 × 10⁻⁴. Source: Annona squamosa, stem bark.

squamoxinone C*42 (reported as a cis and trans mixture) (C35H64O7, MW624)

13. (2,4-cis)-squamoxinone C
14. Position 11 17 18 21 22
15. 1H (δ) 3.58 m 3.39 m 3.82 m 3.87 m 3.82 m
16. 13C (δ) 71.84 74.28 83.18 82.14 71.52
17. Position 11 17 18 21 22
18. 1H (δ) 3.58 m 3.39 m 3.82 m 3.87 m 3.82 m
19. 13C (δ) 71.84 74.28 83.18 82.14 71.52
14. (2,4-trans)-squamoxinone C
15. White wax. [α]D: -13.3° (c 0.023, CH₂Cl₂). UV (λmax, MeOH, nm): 207 (log ε 3.35). IR (λmax, film, cm⁻¹): 339O, 2921, 2851, 177O, 1705, 147O MS: EIMS m/z 389, 337, 319, 301, 255. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀ 9.7 × 10⁻², A-549 ED₅₀ 2.1 × 10⁻¹, MCF-7 ED₅₀ 1.1 × 10⁻³, HT-29 ED₅₀ 3.5 × 10⁻¹, A-498 ED₅₀ 6.7 × 10⁻³, PC-3 ED₅₀ 2.24, PAC-2 ED₅₀ 9.5 × 10⁻³. Source: Annona sauamosa. stem bark.
15. 4-deoxyannomontacin47 (C37H68O6, MW608)

Position 10 17 18 21 22 1H (δ) 3.58 m 3.40 q 3.80 q 3.80 q 3.40 q 13C (δ) 71.88 74.01 82.66 82.61 74.01

White wax. [α]D: +10.9° (c 0.060, CHCl₃). UV (λmax, MeOH, nm): 228 (log ε 2.86). IR (νmax, film, cm⁻¹): 3443, 2921, 2850, 2360, 1742, 1455, 1374, 1318, 1191, 1068, 1028. MS: EIMS m/z 413, 395, 377, 359, 391, 373, 339, 321, 303, 269, 251, 225. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR), TMS (EIMS), peracetate (¹H NMR). Biological activities (μg/mL): BST LC₅₀ 1.3 × 10⁻¹, A-549ED₅₀ 6.5 × 10⁻⁷, MCF-7 ED₅₀ 5.8 × 10⁻⁷, HT-29ED₅₀ 1.4 × 10⁻¹, A-498ED₅₀ 1.5 × 10⁻¹, PC-3ED₅₀ 1.7 × 10⁻¹, PACA-2ED₅₀ 1.0 × 10⁻⁵. Source: Goniothalamus giganteus, stem bark.