534
Adjacent Bis-THF Acetogenins (Continued)
110. membrarollin137 (C35H62O6 MW578)
Position 13 14 17 18 21 22
1H (δ) 3.40 dt 3.81 m 3.87 m 3.87 m 3.90 m 3.85 m13C (δ) 74.00 83.02 81.10 80.99 83.02 71.91
White wax. [α]D: +10° (c O.8, MeOH). UV (λmax, MeOH, nm): 210 (log ε 3.95). IR (νmax, film, cm⁻¹): 3370, 2940, 2880, 1750, 1456, 1380, 1039. MS: EIMS m/z 578, 560, 542, 436, 407, 390, 337, 319, 311, 267, 241, 223, 171, 153, 111, 97. NMR: ¹H NMR (400MHz, CDCl₃), ¹³C NMR (100MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR), p-bromophenylurethane (¹H NMR). Biological activities: NADH oxidase IC₅₀O.3nM. Source: Rollinia membranacea, seeds.
111. guanaconne138 (C37H64O7 MW620)
Position 10 15 16 19 20 23 24
1H (δ) - 3.39 m 3.78 m 3.92 m 3.78 m 3.78 m 3.84 m13C (δ) 211.46 73.86 83.23 82.50 82.25 82.79 71.19
Colorless wax. [α]D: +22° (c 1, EtOH). UV (λmax, MeOH, nm): 208 (log ε 3.83). IR (νmax, film, cm-1): 3416, 2922, 1751, 1647, 1548, 1066 MS: EIMS m/z 449, 379, 361, 311, 309, 293, 291, 241, 223, 195. NMR: 1H NMR (400MHz, CDCl3), 13C NMR (100MHz, CDCl3). Derivatives: per-MTPA esters (1H NMR). Biological activities: NADH oxidase IC50
1.5nM Source: Annona spraguei, seeds.
Nonadjacent Bis-THF Acetogenins
112. goniotriocin*39 (C37H65O8, MW636)
Position 10 13 14 17 20 22
1H (δ) 3.88 m 3.75 q 3.41 dt 3.80 dt 4.62 ddd
13C (δ) 79.3 81.9 74.7 82.7 73.4 209.6
White wax. [α]D: +10.0° (c 0.03, CHCl₃). IR (νmax, film, cm⁻¹): 3378, 2925, 2853, 1750, 1718, 1458, 1066. MS: CIMS (isobutane) m/z 637, 619, 601, 583. EIMS m/z 425, 407, 389, 381, 371, 363, 345, 339, 337, 321, 281, 263, 245, 197, 141. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀ 27, A-549 ED₅₀ 3.3 × 10⁻², MCF-7 ED₅₀ 3.3 × 10⁻⁵, HT-29 ED₅₀ 1.2 × 10⁻³, A-498 ED₅₀ 1.1, PC-3 ED₅₀ 2.6 × 10⁻¹, PACA-2 ED₅₀ 1.4. Source: Goniothalamus giganteus, stem bark.
113. trilobalicin*119 (C35H62O8, MW610)
| Position | 10 | 13 | 14 | 17 | 18 | 21 | 22 |
|---|
| 1H (δ) | 3.87 m | 3.80 m | 3.41 m | 3.41 m | 3.86 m | 3.87 m | 3.80 m |
|---|
| 13C (δ) | 79.3 | 82.0 | 74.4 | 74.6 | 83.3 | 82.2 | 71.6 |
|---|
White wax. [α]D: +13.6° (c 0.125, CHCl_{3}). IR (νmax, film, cm^{-1}): 3333, 2919, 2866, 1738, 1594, 1456, 1398, 1116 MS: EIMS m/z 585, 545, 495, 455, 405, 365, 353, 313, 275, 263, 223, 213, NMR: 1H NMR (500 MHz, CDCl_{3}), 13C NMR (125 MHz, CDCl_{3}). Derivatives: per-MTPA esters (1H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC50 5.8, A-549 ED50 5.8 × 10-8, MCF-7 ED50 1.6 × 10-7, HT-29 ED50 2.3, A-498 ED50 6.0 × 10-3, PC-3 ED50 9.8 × 10-1, PAC-2 ED50 2.8 × 10-1. Source: Asimina triloba, stem bark.
gigantecinone126 (reported as a cis and trans mixture) (C37H66O8, MW638)
cis/trans