538
Non-THF or THP Acetogenins (Continued)
131. diepomuricanin B132 (C35H62O4, MW546)
White wax. [α]D: +10° (c 0.75, CHCl₃). UV (λmax, MeOH, nm): 208 IR (νmax, film, cm⁻¹): 3400, 2910, 2845, 1745. MS: EIMS m/z 323, 293, 279, 97. NMR: ¹H NMR (200 MHz, CDCl₃), ¹³C NMR (50 MHz, CDCl₃). Source: Rollinia membranacea, seeds. 132. tonkinelin¹³³ (C₃₇H₇₀O₄, MW 578)
13 C (δ) 74.53 74.53
White amorphous powder. Mp: 64–66°C. [α]D: +14.5° (c O,07, CHCl₃). IR (νmax, film, cm⁻¹): 3341, 2915, 2848, 1742, 1469. MS: EIMS m/z 579, 561, 543, 335, 323, 209, 195, 181, 167, 153, 139, 125, 111, 97. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: acetonide (¹H NMR), TMS (EIMS). Biological activities (μg/mL): HL-60IC₅₀
1.0, HCT-8IC₅₀ 6.7, KB IC₅₀ > 10, A2780IC₅₀ > 10 Source: Uvaria tonkinesis, root bark.
133. annoijahnin12 (C35H66O5, MW
Position 10 17 18 21 22
Waxy solid. Mp: 70–72°C. [α]D: +15.0° (c 0.008, MeOH). UV (λmax, MeOH, nm): 220 (log ε 3.53). IR (νmax, film, cm⁻¹): 3360, 2918, 2897, 1737, 1703, 1648, 1467, 1282, 1199, 669. MS: EIMS m/z 367, 337, 319, 307, 283, 265, 253, 235, 223, 125, 97. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: acetonide (¹H NMR), per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀ 1.1 × 10¹, A-549 ED₅₀ 1.5, MCF-7 ED₅₀ 2.8, HT-29 ED₅₀ 5.9 × 10⁻², A-498 ED₅₀ 4.9, PC-3 ED₅₀ 1.6 × 10⁻², PACA-2 ED₅₀ 2.3 × 10⁻². Source: Annona jahnii, twigs.
Nonclassical Acetogenins
muconin9(C37H67O7 MW622)
muconin 9(C37H67O 7, MW622)
Position 12 13 17 18 21 22
1H (δ) 3.43 m 3.16 m 3.31 m 3.90 m 3.80 m 3.38 m13C (δ) 74.2 80.9 80.0 81.2 82.8 74.1
White wax. MS: EIMS m/z 405, 387, 353, 335, 317, 269, 141. NMR:1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3). Derivatives: per-MTPA esters (1H NMR), TMS (EIMS). Biological activities (μg/mL): A-549 ED50 4.5 × 10-3, MCF-7 ED50 2.4 × 10-4, HT-29 ED50 3.9 × 10-1, A-498 ED50 1.8 × 10-1, PC-3 ED50 5.8 × 10-1, PAC-2 ED50 5.4 × 10-4. Source: Rollinia mucosa leaves.
135. pyranicin10 (C35H64O7, MW596)
135. pyranicin10 (C35H64O7, MW596)
| Position | 10 | 15 | 16 | 19 | 20 |
|---|
| 1H (δ) | 3.60 m | 3.46 dt | 3.19 ddd | 3.61 m | 3.34 ddd |
|---|
| 13C (δ) | 71.7 | 73.9 | 81.1 | 66.1 | 80.0 |
|---|
White amorphous wax. [α]D: -9.7° (c 0.008, CHCl_{3}). UV (λmax, MeOH, nm): 216 (log ε 3.32). IR (νmax, film, cm^{-1}): 3418, 2928, 2854, 1748, 1456, 1319, 1086. MS: EIMS m/z 426, 309, 291, 273, 269, 251, 241, 223, 205, 141. NMR: 1H NMR (500 MHz, CDCl_{3}), 13C NMR (125 MHz, CDCl_{3}). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): BST LC_{50} 3 × 10^{-1}, A-549 ED_{50} 2.8 × 10^{-1}, MCF-7 ED_{50} 3.9 × 10^{-1}, HT-29 ED_{50} 1.2, A-498 ED_{50} 1.8 × 10^{-1}, PC-3 ED_{50} 4.1 × 10^{-1}, PACA-2 ED_{50} 1.3 × 10^{-3}. Source: Goniothalamus giganteus, stem bark.