Table 4. (Continued)

Nonclassical Acetogenins (Continued)

  1. 136. pyragonicin10 (C35H64O7, MW 596)

Position 10 13 14 17 18 1H (δ) 3.63 m 3.50 dt 3.24 ddd 3.63 m 3.36 ddd 13C (δ) 71.5 74.4 80.9 66.0 79.8

<table><tr><td>1H (δ)</td><td>3.63 m</td><td>3.50 dt</td><td>3.24 ddd</td><td>3.63 m</td><td>3.36 ddd</td></tr><tr><td>13C (δ)</td><td>71.5</td><td>74.4</td><td>80.9</td><td>66.0</td><td>79.8</td></tr></table>

  1. White amorphous wax. [α]D: -25.6° (c 0.008, CHCl_{3}). UV (λmax, MeOH, nm): 215 (log ε 3.71). IR (νmax, film, cm^{-1}): 3479, 2920, 2851, 1748, 1456, 1318, 1084. MS: EIMS m/z 381, 297, 281, 279, 263, 245, 241, 223, 205, 141. NMR: 1H NMR (500 MHz, CDCl_{3}), 13C NMR (125 MHz, CDCl_{3}). Derivatives: peracetate (1H NMR), per-MTPA esters (1H NMR), formal acetal (1H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC50 9 × 10^{-1}, A-549 ED50 2, MCF-7 ED50 1.6, HT-29 ED50 2.8, A-498 ED50 1.3 × 10^{-1}, PC-3 ED50 1.2 × 10^{-1}, PAC-2 ED50 5.8 × 10^{-2}. Source: Goniothalamus giganteus, stem bark. 137. jimenezin11 (C37H66O7, MW 622)

Position 15 16 19 20 23 24 1H (δ) 3.35 m 3.90 m 3.94 m 3.24 ddd 3.28 ddd 3.00 ddd 13C (δ) 73.9 82.4 80.9 79.0 70.6 82.3

Yellow oil. [α]D: +8.3° (c 1.2, MeOH). UV (λmax, MeOH, nm): 210.5 (log ε 3.97). IR (νmax, film, cm⁻¹): 3100–3650, 3023, 2928–1750, 1641, 1423, 1215, 1028, 930. MS: EI-MS (TMS) m/z 525, 455, 453, 383, 313, 293, 223, 213, 123. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR), TMS (EI-MS). Biological activities (μg/mL): BST LC₅₀ 5.7 × 10⁻³, A-549 ED₅₀ 1.6 × 10⁻², MCF-7 ED₅₀ >10⁻¹, HT-29 ED₅₀ 4.3 × 10⁻³, A-498 ED₅₀ 4.9 × 10⁻², PC-3 ED₅₀ 2.8 × 10⁻⁴, PACA-2 ED₅₀ 1.7 × 10⁻⁴. Source: Rollinia mucosa, seeds.

539

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