524

Table 4. (Continued)

60. 60. tonkinin C*66 (C39H68O8, MW664) Mono-THF Acetogenins (Continued)

Mono-THF Acetogenins (Continued)

Position 5 13 14 15 19 20 1H (δ) --- 3.36 m 1.53 m 5.08 m 3.84 m 3.84 m 13C (δ) 209.40 70.37 38.58 71.54 82.47 71.44

61. Amorphous powder. Mp: 40–42°C. [α]D: +10.8° (c Q119, CHCl₃). IR (ν_max, film, cm⁻¹): 3430, 2919, 2850, 1759, 1723, 1468, 1377, 1255, 1077, 1030 MS: EIMS m/z 586, 568, 479, 465, 461, 447, 405, 395, 387, 351, 335, 269, 181, 168, 153, NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: peracetate (¹H NMR), per-MTPA esters (¹H NMR), TMS (EIMS). Biological activities (μg/mL): HCT-81C50 8.6 × 10⁻¹, HL-60IC50 4.2 × 10⁻⁴, KB IC₅₀ > 10, A2780 IC₅₀ > 10. Source: Uvaria tonkinensis, roots.

Position 5 15 17 18 21 22

1H (δ) 3.60 m 3.80 m 3.73 m 3.90 m 3.90 m 3.90 m

13C (δ) 70.83 68.78 71.89 83.07 82.28 71.67

Powder. Mp: 97–99°C. [α]D: +26.92° (c O.O.26, CHCl₃). IR (νmax, film, cm⁻¹): 3379, 2918, 2850, 1741. MS: EIMS m/z 407, 389, 355, 337, 311, 293, 269, 155. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: TMS (EIMS). Source: Uvaria tonkinesis, roots.

62. 62. tonkinesin B*66 (C37H68O7, MW624)

Position 5 15 17 18 21 22

1H (δ) 3.81 m 3.81 m 3.75 m 3.88 m 3.88 m 3.41 m

13C (δ) 70.86 68.61 71.56 82.75 82.61 74.10

Powder. Mp: 80–81 °C. [α]D: +24.5° (c O.O.49, CHCl₃). IR (νmax, film, cm⁻¹): 3433, 2920, 2850, 1747, 1082 MS: EIMS m/z 625, 607, 589, 571, 553, 425, 407, 389, 371, 355, 337, 319, 311, 293, 269, 155. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: TMS (EIMS). Source: Uvaria tonkinesis, roots.

63. 63. tonkinesin C66(C39H70O8, MW666)

Position 5 15 17 18 21 22

1H (δ) 3.55 m 3.36 m 5.06 m 3.84 m 3.84 m 3.84 m13C (δ) 70.73 70.39 71.35 82.79 82.66 71.54

Oil. [α]D: +25.2° (c 0.651, CHCl₃). IR (νmax, film, cm⁻¹): 3465, 2923, 2852, 1737, 1245. MS: EIMS m/z 467, 407, 389, 371, 337, 319, 311, 301, 293, 155. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: TMS (EIMS). Source: Uvaria tonkinesis, roots.

64. 64. annopentocin A116(C35H64O8, MW612)

Position 10 12 15 16 19 20

1H (δ) 3.80 m 4.18 m 3.91 m 3.45 m 3.42 m 3.42 m13C (δ) 71.6 80.0 82.4 73.9 74.3 74.5

White amorphous powder. [α]D: +1Z (c14, CHCl3). UV (λmax, MeOH, nm): 215 (ε900). IR (νmax, film, cm⁻¹): 338, 290, 2855, 1745, 1470. MS: EIMS (TMS) m/z 701, 611, 521, 503, 469, 431, 413, 385, 379, 341, 323, 295, 289, 271, 213, 181. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: acetonide (¹H NMR), per-MTPA esters (¹H NMR), peracetate (¹H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC₅₀ 8.9, A-549 ED₅₀ 1.7 × 10⁻¹, MCF-7 ED₅₀ 1.8 × 10⁴, HT-29 ED₅₀ 1.6, A-498 ED₅₀ 6.1 × 10⁻¹, PC-3 ED₅₀ 1.1, PAC-2 ED₅₀ 3.6 × 10⁻². Source: Annona muricata, leaves