516

Table 4. (Continued)

Mono-THF Acetogenins (Continued) ns mixture) (C37H68O7, MW624)

annomontacinone47 (reported as a cis and trans mixture) (C37H68O7, MW624)

  1. (2,4-cis)-annomontacinone
  2. Position 10 17 18 21 22
  3. 1 H (δ) 3.58 m 3.40 q 3.80 q 3.80 q 3.40 q
  4. 13 C (δ) 71.86 74.00 82.64 82.57 74.06
  5. Position 10 17 18 21 22
  6. 1 H (δ) 3.58 m 3.40 q 3.80 q 3.80 q 3.40 q
  7. 13 C (δ) 71.86 74.00 82.64 82.57 74.06
  8. (2,4-trans)-annomontacinone
  9. Whitish wax. [α]D: +13.6° (c 0.022, CHCl_{3}). IR (νmax, film, cm^{-1}): 3433, 2920, 2850, 1754, 1717, 1550, 1460, 1182, 1075, 727 NMR: 1H NMR (500 MHz, CDCl_{3}), 13C NMR (125 MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR), per-MTPA esters (^{1}H NMR), formal acetal (^{1}H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC50 3.1 × 10^{-1}, A-549 ED50 2.6, MCF-7 ED50 3.2, HT-29 ED50 2.6 × 10^{-1}, A-498 ED50 1.4, PC-3 ED50 1.0, PAC-2 ED50 6.8 × 10^{-1}. Source: Goniothalamus giganteus, stem bark.
  10. muricoreacin110 (C35H64O9, MW628)

Position8101215161920
1H ( \delta )3.86 m4.06 m4.15 m3.90 m3.49 m3.59 m3.59 m
13C ( \delta )71.672.279.182.373.874.874.6

White solid. [α]D: +1.6° (c 0.06, CHCl_{3}). UV (λmax, MeOH, nm): 220 (log ε 3.65). IR (νmax, film, cm^{-1}): 3347, 2916, 2849, 1743, 1470. MS: EIMS m/z 429, 411, 393, 375, 357, 341, 339, 323, 305, 287, 269, 257, 251, 239, 221, 213, 203, 199, 195, 181, 177, 141, 123. NMR: ^1H NMR (500 MHz, CDCl_{3}), ^13C NMR (125 MHz, CDCl_{3}). Biological activities (μg/mL): BST LC50 19, A-549 ED50 2.3 × 10-1, MCF-7 ED50 1.3, HT-29 ED50 5.7 × 10-1, A-498 ED50 7.1 × 10-1, PC-3 ED50 2.5 × 10-2, PAC-2 ED50 2.3 Source: Annona muricata, leaves.

  1. 19. murihexocin*110(C37H68O7, MW628)

White solid. [α]D: +37.5° (c QO4, CHCl_{3}). UV (λmax, MeOH, nm): 220 (log ε 3.69). IR (νmax, film, cm^{-1}): 3367, 2915, 2849, 1743, 1474. MS: EIMS m/z 429, 411, 393, 375, 357, 341, 339, 323, 305, 299, 287, 281, 269, 263, 251, 245, 211, 199, 193, 181, 163, 141, 123. NMR: 1H NMR (500MHz, CDCl_{3}), 13C NMR (125 MHz, CDCl_{3}). Biological activities (μg/mL): BST LC_{50} 10, A-549 ED_{50} 1.1, MCF-7 ED_{50} 3.8, HT-29 ED_{50} 1.3, A-498 ED_{50} 2.5, PC-3 ED_{50} 8.6 \times 10^{-1}, PAC-2 ED_{50} 4.9 \times 10^{-1}. Source: Annona muricata, leaves.

  1. 20. glacin A^{25} (C_{35}H_{64}O_{7}, MW596)

Position1217182122
1H (δ)3.60 m3.41 m3.80 m3.80 m3.41 m
13C (δ)71.8274.0782.6582.5973.98

Whitish waxy solid. [α]D: +6.0° (CHCl₃). UV (λmax, MeOH, nm): 218 (log ε 3.83). IR (νmax, film, cm-1): 3461, 2919, 2851, 1734, 1717, 1464, 1318, 1203, 1075. MS: EIMS m/z 425, 407, 355, 337, 319, 301, 269, 251, 241, 233, 223, 171, 141. NMR: 1H NMR (500 MHz, CDCl₃), {}^{13}C NMR (125 MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities μg/mL): BST LC50 1.1 × 10-1, A-549 ED50 1.5, MCF-7 ED50 4.4 × 10-3, HT-29 ED50 2.3, A-498 ED50 1.3, PC-3 ED50 9.8 × 10-3, PAC-2 ED50 8.6 × 10-3. Source: Annona glabra, leaves.