526

Table 4. (Continued)

  1. 70. uvaribonin*134 (C39H70O8 MW666) Mono-THF Acetogenins (Continued)

Position 5 15 17 18 21 22 1H (δ) 3.58 m 3.40 m 5.10 m 3.82 m 3.82 m 3.40 m 13C (δ) 70.8 70.1 71.7 82.2 82.9 74.1

1H (δ) 3.58 m 3.40 m 5.10 m 3.82 m 3.82 m 3.40 m13C (δ) 70.8 70.1 71.7 82.2 82.9 74.1 13C (δ) 70.8 70.1 71.7 82.2 82.9 74.1

  1. Waxy solid. Mp: 50–52 °C. [α]D: +13° (c 0.06, CHCl_{3}). IR (νmax, film, cm^{-1}): 3450, 2935, 2862, 1755, 1742, 1725. MS: EIMS (TMS) m/z 588, 570, 552, 467, 407, 397, 389, 371, 337, 319, 311, 301, 293, 269, 251, 199, 181, 155, 137, 111, 109, 97. NMR: ^{1}H NMR (500MHz, CDCl_{3}), ^{13}C NMR (125MHz, CDCl_{3}). Derivatives: TMS (EIMS). Source: Uvaria boniana, bark. 71. uvaribonianin*134 (C37H66O8 MW644)

Position 13 15 16 19 201H (δ) 3.41 m 5.10 m 3.82 m 3.82 m 3.40 m13C (δ) 70.1 71.7 82.8 82.9 74.1

  1. Waxy solid. [α]D: +13° (c Q06, CHCl_{3}). IR (νmax, film, cm^{-1}): 3480, 2928, 2830, 1755. MS: EIMS (TMS) m/z 562, 544, 526, 423, 363, 353, 345, 293, 275, 269, 267, 251, 249, 199, 181, 111, 97. NMR: 1H NMR (500MHz, CDCl_{3}), 13C NMR (125MHz, CDCl_{3}). Derivatives: TMS (EIMS). Source: Uvaria boniana, bark.
  2. 72. uvarigin135 (C37H68O6 MW608)

Position 15 16 19 20 23 24 28 291H (δ) 3.36 m 3.84 m 3.84 m 3.84 m 3.91 m 3.82 m 3.36 m 3.36m13C (δ) 73.9 83.3 82.5 82.0 82.6 71.4 74.0 74.3

Crystal. Mp: 85–86°C. [α]D: +30.5° (c 0.02, MeOH). IR (νmax, film, cm⁻¹): 3445, 2915, 2850, 1745, 1630, 1460, 1065 MS: EIMS (TMS) m/z 554, 409, 391, 373, 355, 343, 339, 321, 295, 269, 251, 111, 83 NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: TMS (EIMS). Source: Uvaria grandiflora, roots. Adjacent Bis-THF Acetogenins 73. uvarigrandin A135 (C37H66O7 MW622)

  1. 73. uvarigrandin A135 (C37H66O7 MW622) Adjacent Bis-THF Acetogenins

  1. Waxy solid. Mp: 30–33 °C. [α]D: +28.5° (c Q11, MeOH). 1R (νmax, film, cm-1): 3450, 2930, 1760, 1660, 1470, 1325, 1070 MS: EIMS (TMS) m/z 554, 409, 391, 373, 355, 343, 339, 321, 295, 269, 251, 111, 83. NMR:1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3). Derivatives: TMS (EIMS). Source: Uvaria grandiflora, roots. 74. spinencin27 (C37H66O8, MW638)

Position1516192023242829
1H (δ)3.36 m3.84 m3.84 m3.84 m3.91 m3.82 m3.36 m3.36 m
13C (δ)73.983.382.582.082.671.474.074.3

Transparent oil. [α]D: +24° (c O1, CHCl_{3}). UV (λmax, MeOH, nm): 204.6 (log ε 3.86). IR (νmax, film, cm^{-1}): 3785, 3677, 2995, 2860, 1751. NMR: 1H NMR (400MHz, CDCl_{3}), 13C NMR (50MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR), acetonide (^{1}H NMR). Source: Annona spinescens, seeds.