Invited Review
Journal of Natural Products, 1999, Vol. 62, No. 3 535
Table 4. (Continued)
(2,4-cis)-gigantecinone Nonadjacent Bis-THF Acetogenins (Continued)
Position 1H (δ) 10 13 14 17 18 21 22
13C (δ) 79.2 82.0 74.0 74.2 82.7 82.7 74.4
(2,4-trans)-gigantecinone
Position 1H (δ) 10 13 14 17 18 21 22
13C (δ) 79.2 82.0 74.0 74.2 82.7 82.7 74.4
White wax. [α]D: +23.3° (c 0.15, CHCl_{3}). IR (νmax, film, cm^{-1}): 3507, 3389, 2908, 2837, 1749, 1708, 1461, 1190, 1167, 1049. MS: EIMS m/z 439, 421, 403, 369, 351, 339, 333, 321, 303, 281, 269, 263, 251, 199, 141. 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). Biological activities (μg/mL): BST LC50 3.3, A-549 ED50 2.1 × 10-1, MCF-7 ED50>1, HT-29 ED50>1, A-498 ED50 2.1 × 10-1, PC-3 ED50 1.1 × 10-3, PAC-2 ED50>1. Source: Goniothalamus giganteus, stem bark.
Non-THF or THP Acetogenins
116. montecristin127 (C37H66O4, MW574)
Position 13 14 17 18 21 221H (δ) 3.42 m 3.42m 5.41 m 5.37 m 5.41 m 5.37 m13C (δ) 73.93 74.35 128.78 130.43 129.20 130.04
<table><tr><td>1 H ( \delta )</td><td>3.42 m</td><td>3.42m</td><td>5.41 m</td><td>5.37 m</td><td>5.41 m</td><td>5.37 m</td></tr><tr><td>13 C ( \delta )</td><td>73.93</td><td>74.35</td><td>128.78</td><td>130.43</td><td>129.20</td><td>130.04</td></tr></table>
White wax. Mp: 62–65°C. [α]D: +25° (c 0.1, CHCl₃). UV (λmax, MeOH, nm): 211.7 (log ε 3.80). IR (νmax, film, cm⁻¹): 3300, 2900, 2840, 1740, 1650, 1120, 1080, 1030. NMR: ¹H NMR (400MHz, CDCl₃), ¹³C NMR (50MHz, CDCl₃). Derivatives: acetonide (¹H NMR). Source: Annona muricata roots.
Derivatives: acetonide 1 HNMR. Source: Annona muricata, roots.
117. muridienin-1128 (C35H62O2, MW514)
Position 13 14 17 181H (δ) 5.38-5.41 m 5.38-5.41 m 5.38-5.41 m 5.38-5.41 m13C (δ) 128.96 130.20 129.44 130.20
1H (δ) 5.38-5.41 m 5.38-5.41 m 5.38-5.41 m 5.38-5.41 m13C (δ) 128.96 130.20 129.44 130.20
118. muridienin-2^{128} (C_{37}H_{66}O_{2}, MW542)
Position 15 16 19 201H (δ) 5.38-5.41 m 5.38-5.41 m 5.38-5.41 m 5.38-5.41 m13C (δ) 128.96 130.20 129.44 130.20
1H (δ) 5.38-5.41 m 5.38-5.41 m 5.38-5.41 m 5.38-5.41 m13C (δ) 128.96 130.20 129.44 130.20
donnaienin D 34 (reported as an epimeric pair) (C 37 H 66 O 9, MW672)
threo threo 35、33OH
32 OH OH OH OH OAc OH
20 16 10 4 2 0
19 15 10 4 1 1
OH OH OH OH OH OH
donnaienin D
Position 4 10 15 16 19 20 34
1 H ( \delta ) 5.05 m 3.62 m 3.46 m 3.46 m 3.46 m 3.46 m ---
13 C ( \delta ) 71.3 69.4 73.7 73.6 73.2 73.1 104.8
34-epi-donnaienin D
Position 4 10 15 16 19 20 34
1 H ( \delta ) 5.05 m 3.62 m 3.46 m 3.46 m 3.46 m 3.46 m ---
13 C ( \delta ) 71.2 69.5 73.6 73.3 73.2 73.1 104.8
White amorphous powder. Mp: 78–81 °C. [α]D: +8.6° (c O.21, MeOH). IR (νmax, film, cm⁻¹): 3360, 2918, 2849, 1751, 1468 MS: EIMS m/z 473, 413, 395, 377, 359, 341, 385, 367, 349, 325, 307, 307, 289, 287, 269, 251, 199, 139, 121. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: phenylhydrazone (¹H NMR), per-MTPA esters (¹H NMR), acetonide (¹H NMR). Biological activities (μg/mL): KB IC₅₀ >10. HCT-8 IC₅₀ >10, Bel IC₅₀ >10. Source: Goniothalamus donnaiensis, roots.