528
80. (2,4-trans)-9-hydroxyasimicinone
Position 9 15 16 19 20 23 24
1H (δ) 3.58 m 3.39 m 3.85 m 3.85 m 3.85 m 3.85 m 3.85 m 3.39 m
13C (δ) 71.64 74.05 83.06 81.79 81.76 83.16 73.96
White wax. [α]D: +19.3° (c 0.26, CH₂Cl₂). UV (λmax, MeOH, nm): 203 (log ε 2.98). IR (λmax, film, cm⁻¹): 3460, 2930, 1769, 1714, 1463 MS: EIMS m/z 227, 209, 309, 291, 273, 379, 361. NMR: ¹H NMR (500 MHz, CDCl₃), ¹³C NMR (125 MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀ 3.5 × 10⁻¹, A-549 ED₅₀ 7.7 × 10⁻², MCF-7 ED₅₀ 1.2 × 10⁻³, HT-29 ED₅₀ 1.4, A-498 ED₅₀ 3.6 × 10⁻², PC-3 ED₅₀ 1.6 × 10⁻¹, PAC-2 ED₅₀ 1.7 × 10⁻⁴. Source: Annona squamosa, stem bark.
81. glaucanetin* 117(C 37 H 66 O 7, MW622)
Position 13 14 17 18 21 22
1H (δ) 3.39 m 3.85 m 3.85 m 3.85 m 3.85 m 3.39 m
13C (δ) 74.07 83.15 81.74 81.74 83.15 74.07
Solid. [α]D: +15° (c O,2O, MeOH). UV (λmax, MeOH, nm): 209 (log ε 3.94). IR (νmax, film, cm-1): 3349, 2930, 2857, 1745, 1652, 1515, 1464, 1320, 1204, 1069. MS: EIMS m/z 387, 335, 321, 317, 283, 269, 265, 247, 171, 141, 97. NMR: 1H NMR (200MHz, CDCl3), 13C NMR (50MHz, CDCl3). Derivatives: peracetate (1H NMR), TMS (EIMS). Source: Annona glauca, seeds.
82. 10-hydroxyglaucanetin*117 (C37H68O8, MW638)
Position 10 13 14 17 18 21 22
1H (δ) 3.60 m 3.39 m 3.85 m 3.85 m 3.85 m 3.85 m 3.39 m13C (δ) 71.55 74.04 82.82 81.71 81.83 83.19 74.04
Solid. [α]D: +17° (c O23, MeOH). UV (λmax, MeOH, nm): 210 (log ε 4.00). IR (νmax, film, cm-1): 3423, 2933, 2859, 1754, 1458, 1320, 1066. MS: EIMS m/z 421, 403, 385, 351, 339, 333, 321, 317, 281, 269, 263, 251, 245, 241, 205, 199, 181, 141, 97. NMR: 1H NMR (200MHz, CDCl 3), 13C NMR (50MHz, CDCl 3). Derivatives: peracetate (1H NMR), TMS (EIMS). Source: Annona glauca, seeds.
83. bulladecin *118 (C37H67O8, MW638)
Position 12 15 16 19 20 23 241H (δ) 3.93 m 3.87 m 3.87 m 3.87 m 3.47 m 3.60 m 3.60 m13C (δ) 79.9 81.2 82.1 82.7 74.2 74.5 74.7
White solid. [α]D: +11° (c O.2O, MeOH). UV (λmax, MeOH, nm): 214 (log ε 4.85). MS: EIMS m/z 449, 431, 413, 379, 361,
291, 141, 123, 97. NMR:1H NMR (200MHz, CDCl3),13C NMR (50MHz, CDCl3). Derivatives: per-acetate (1H NMR), acetonide (1H NMR). Source: Annona atemoya, seeds.
84. atemotetrolin *118 (C37H67O8, MW638)
| Position | 15 | 16 | 19 | 20 | 23 | 24 | 28 | 29 |
|---|
| 1H (δ) | 3.40 m | 3.82 m | 3.92 m | 3.92 m | 3.92 m | 3.87 m | 3.40 m | 3.40 m |
|---|
| 13C (δ) | 74.2 | 83.2 | 82.6 | 82.1 | 82.8 | 71.4 | 74.2 | 74.2 |
|---|
Transparent oil. [α]D: +23° (c 0.20, MeOH). UV (λmax, MeOH, nm): 219 (log ε 3.54). IR (νmax, film, cm-1): 3447, 2927, 2851, 1756. MS: EIMS m/z 567, 533, 519, 501, 495, 483, 465, 435, 417, 399, 365, 347, 255, 237, 185, 167, 149, 101. NMR:
1H NMR (200 MHz, CDCl3),13C NMR (50 MHz, CDCl3). Derivatives: peracetate (1H NMR), acetonide (1H NMR).
Source: Annona atemova, seeds.
trilobacinone119 (reported as a cis and trans mixture) (C37H66O7, MW622)
cis/trans